[ CAS No. 766-49-4 ] {[proInfo.proName]}

Name: 766-49-4|1-Ethynyl-2-fluorobenzene|98%
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SKU: A901248
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Quality Control of [ 766-49-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 766-49-4 ]

Product Details of [ 766-49-4 ]

CAS No. :	766-49-4	MDL No. :	MFCD00799540
Formula :	C₈H₅F	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YFPQIXUNBPQKQR-UHFFFAOYSA-N
M.W :	120.12	Pubchem ID :	643358
Synonyms :

Calculated chemistry of [ 766-49-4 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.34
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.42 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	2.27
Log Po/w (WLOGP) :	2.31
Log Po/w (MLOGP) :	3.28
Log Po/w (SILICOS-IT) :	2.89
Consensus Log Po/w :	2.57

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.51
Solubility :	0.373 mg/ml ; 0.0031 mol/l
Class :	Soluble
Log S (Ali) :	-1.91
Solubility :	1.49 mg/ml ; 0.0124 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.71
Solubility :	0.234 mg/ml ; 0.00195 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.48

Safety of [ 766-49-4 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P261-P305+P351+P338	UN#:	1993
Hazard Statements:	H225-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 766-49-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 766-49-4 ]
Downstream synthetic route of [ 766-49-4 ]

[ 766-49-4 ] Synthesis Path-Upstream 1~14

1
[ 766-49-4 ]
[ 445-28-3 ]

Reference： [1] Tetrahedron Letters, 2009, vol. 50, # 24, p. 2973 - 2975
[2] Advanced Synthesis and Catalysis, 2016, vol. 358, # 3, p. 500 - 505

2
[ 401514-42-9 ]
[ 766-49-4 ]

Yield	Reaction Conditions	Operation in experiment
61%	With caesium carbonate In dimethyl sulfoxide at 115℃; Sealed tube; Inert atmosphere	General procedure: Following a modified literature procedure[10] dibromoalkenes S2 (1.0 equiv.), Cs2CO3 (2.5 equiv.) and DMSO (0.1M) are mixed in a sealed tube and heated to 115 °C overnight. The reaction is quenched by pouring the reaction mixture into brine (20 mL/mmol). The resulting mixture is extracted with tert-butyl methyl ether (3x10 mL/mmol) and the combined organic layers are washed with brine (15 mL/mmol) and dried over Na2SO4. Removal of all volatiles gives the crude product which is purified by flash column chromatography to afford the terminal alkynes S3.

Reference： [1] Tetrahedron, 2017, vol. 73, # 33, p. 5023 - 5028

3
[ 178173-84-7 ]
[ 766-49-4 ]

Reference： [1] Synthesis, 1996, # 5, p. 589 - 590

4
[ 187463-12-3 ]
[ 766-49-4 ]

Reference： [1] Russian Journal of Organic Chemistry, 1997, vol. 33, # 8, p. 1065 - 1067

5
[ 446-52-6 ]
[ 766-49-4 ]

Reference： [1] Journal of the American Chemical Society, 1963, vol. 85, p. 3492 - 3496
[2] Tetrahedron, 2017, vol. 73, # 33, p. 5023 - 5028

6
[ 1072-85-1 ]
[ 766-49-4 ]

Reference： [1] Synthesis, 1996, # 5, p. 589 - 590
[2] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 5, p. 1625 - 1632

7
[ 394-46-7 ]
[ 766-49-4 ]

Reference： [1] Journal of the American Chemical Society, 1963, vol. 85, p. 3492 - 3496

8
[ 445-26-1 ]
[ 766-49-4 ]

Reference： [1] Journal of the American Chemical Society, 1963, vol. 85, p. 3492 - 3496

9
[ 348-52-7 ]
[ 766-49-4 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 10, p. 2522 - 2525

10
[ 18944-77-9 ]
[ 766-49-4 ]

Reference： [1] Russian Journal of Organic Chemistry, 1997, vol. 33, # 8, p. 1065 - 1067

11
[ 342-19-8 ]
[ 766-49-4 ]

Reference： [1] Russian Journal of Organic Chemistry, 1997, vol. 33, # 8, p. 1065 - 1067

12
[ 766-49-4 ]
[ 50919-06-7 ]

Reference： [1] Nature Chemistry, 2014, vol. 6, # 1, p. 22 - 27
[2] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17376 - 17379,4
[3] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17376 - 17379
[4] Journal of the American Chemical Society, 2014, vol. 136, # 19, p. 7058 - 7067

13
[ 766-49-4 ]
[ 50919-06-7 ]
[ 75321-85-6 ]

Reference： [1] Nature Chemistry, 2014, vol. 6, # 1, p. 22 - 27

14
[ 766-49-4 ]
[ 171032-87-4 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 4, p. 1110 - 1113
[2] RSC Advances, 2018, vol. 8, # 27, p. 14829 - 14832

[ 766-49-4 ] Synthesis Path-Downstream 1~84

1
[ 766-49-4 ]
1,1′-buta-1,3-diyne-1,4-diylbis(2-fluorobenzene) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium acetate; silver sulfate; In dimethyl sulfoxide; at 90℃; for 9.0h;	General procedure: A mixture of alkyne 1 (0.2 mmol), nano-Pd (0.1 mol% Pd), Ag2SO4(30 mol%), NaOAc (1 equiv), and DMSO (1 mL) was stirred at 90 oC until complete consumption of starting material as judged by TLC. After the mixture was filtered and evaporated, the residue was purified by flash column chromatography to afford the product 2 (petroleum ether or petroleum ether/ethyl acetate).
90%	With piperidine; In toluene; at 60℃; under 760.051 Torr; for 24.0h;	General procedure: A mixture ofcatalyst (PS-TEDETA-CuSO4, 0.05 mmol of Cu), terminal alkyne (0.5 mmol) and piperidine (0.5mmol) in toluene (1.0 mL) was stirred at 60 oC for 24-48 h under air. After cooling, the mixture wasfiltered, and the residue was washed by dichloromethane (2 mL x3). The combined organic phaseswere concentrated in vacuo and the crude products were purified by column chromatography(hexane/AcOEt) to give the corresponding 1,3-diynes.
78%	With N,N,N,N,-tetramethylethylenediamine; copper; In 1,4-dioxane; chloroform; at 50℃;Schlenk technique; Inert atmosphere;	General procedure: Following a modified literature procedure[11] in a flame dried 100 mL-Schlenk tube copper powder (6.4 mg, 0.1 mmol, 5 mol%), TMEDA (47 mg, 0.4 mmol, 20 mol%) and terminal alkyne S3a-d, S4-8, S10 (2.0 mmol, 1.0 equiv.) are suspended in chloroform (1.0 mL) and 1,4-dioxane (0.3 mL). The mixture is stirred at 50 C overnight. After cooling the mixture is diluted with dichloromethane (4 mL) and filtered through a plug of silica (1 cm) and concentrated under reduced pressure.

73%

With copper(II) bis(trifluoromethanesulfonate); 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 25℃;

General procedure: To a 5 mL acetone solution of alkyne (1a: 1 mmol, 0.10 g; 1b: 1 mmol, 0.18 g; 1c: 1 mmol, 0.14g; 1d: 1 mmol, 0.14 g; 1e: 1 mmol, 0.14 g; 1f: 1 mmol, 0.12 g; 1g: 1 mmol, 0.12 g; 1h: 1 mmol,0.12 g; 1i: 1 mmol, 0.12 g; 1j: 1 mmol, 0.13 g; 1k: 1 mmol, 0.13 g; 1l: 1 mmol, 0.18 g; 1m: 1mmol, 0.23 g; 1n: 1 mmol, 0.13 g ), DBU (1 mmol, 0.15 g) and Cu(OTf)2 (5 mmol %, 18 mg) were added and allowed to stir 3-5 hours at rt. When TLC showed full consumption of the starting material, the crude mixture was purified by flash column chromatography on silica gel 60 to obtain the pure product 2.

Reference： [1]Tetrahedron,2016,vol. 72,p. 6996 - 7002
[2]Angewandte Chemie - International Edition,2019,vol. 58,p. 17226 - 17230
Angew. Chem.,2019,vol. 131,p. 17386 - 17390,5
[3]Green Chemistry,2011,vol. 13,p. 843 - 846
[4]Synlett,2016,vol. 27,p. 1232 - 1236
[5]Angewandte Chemie - International Edition,2019,vol. 58,p. 10683 - 10687
Angew. Chem.,2019,vol. 131,p. 10793 - 10797,5
[6]Tetrahedron,2017,vol. 73,p. 5023 - 5028
[7]Tetrahedron Letters,2019,vol. 60,p. 1179 - 1181
[8]Synlett,2001,p. 108 - 110

2
[ 766-49-4 ]
(E)-2,2'-(but-1-en-3-yne-1,4-diyl)bis(fluorobenzene) [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 2584 - 2590
[2]RSC Advances,2015,vol. 5,p. 5004 - 5009
[3]Journal of the American Chemical Society,2001,vol. 123,p. 11107 - 11108
[4]Organometallics,2019,vol. 38,p. 3752 - 3759

3
[ 766-49-4 ]
[ 54-42-2 ]
1-(2-deoxy-β-D-ribofuranosyl)-5-[(2-fluorophenyl)ethynyl]uracil [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 50℃; for 0.08333330000000001h;Microwave irradiation;	General procedure: A mixture comprised of the appropriate alkyne (0.54mmol), Pd(PPh3)4 (20 mg, 0.017 mmol), CuI (3.2 mg, 0.017mmol), triethylamine (47 mul, 0.34 mmol) and 1-(2-deoxy-beta-D-ribofuranosyl) 5-iodouracil (22) (100 mg, 0.28 mmol), in1.0 mL of anhydrous DMF, was irradiated in a microwaveapparatus (200 Watt maximum power) at 50 for 5 minutes.The reaction mixture was concentrated under reducedpressure and the crude residue was purified by flash chromatographyon silica gel. The purified material was dried invacuo to afford the corresponding derivatives 23a-d, 25 in65-83% yields, as colorless foams.2.16.1. 1-(2-Deoxy-beta-D-ribofuranosyl)-5-[(2-fluorophenyl)ethynyl]uracil (23a)80 mg, 83%; [alpha]D22 = -2 (c 0.25, CH3OH); Rf = 0.19(CH2Cl2/CH3OH 9:1); lambdamax 343 nm (epsilon 6329); 1HNMR (300MHz,CD3OD): delta 8.45 (s, 1H, H-6), 7.56-7.53 (m, 1H, ArH),7.40-7.36 (m, 1H, ArH), 7.18-7.12 (m, 2H, ArH), 6.27 (t,1H, J1-2a = 13.0 Hz, J1-2b = 6.5 Hz H-1), 4.44-4.41 (m, 1H,H-4), 3.95-3.93 (m, 1H, H-3), 3.85 (dd, 1H, J4-5b = 2.9 Hz,J5a-5b = 12.0 Hz, H-5b), 3.76 (dd, 1H, J4-5a = 3.3 Hz, J5a-5b= 12.0 Hz, H-5a), 2.37-2.25 (m, 1H, H-2); 13C NMR (75.5MHz, CD3OD): delta 161.58, 160.43, 150.74, 142.52, 133.89,126.74, 123.88, 115.19, 109.24, 100.92, 93.45, 93.02, 89.07,86.45, 70.51, 61.29, 40.56; Mass (M+H)+: 347.10; Anal.Calcd. for C17H15FN2O5: C, 58.96; H, 4.37; F, 5.49; N,8.09% Found: C, 58.16; H, 4.17; F, 5.69; N, 8.19%.

Reference： [1]Medicinal Chemistry,2020,vol. 16,p. 368 - 384
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 1041 - 1049

4
[ 445-26-1 ]
[ 766-49-4 ]

Reference： [1]Journal of the American Chemical Society,1963,vol. 85,p. 3492 - 3496

5
[ 5437-67-2 ]
[ 766-49-4 ]
[ 668970-74-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	In 1,3,5-trimethyl-benzene at 150℃; for 12h;	A Preparation of 5-(2-fluorophenyl)isoxazole-3-carboxylic acid 1-ethynyl-2-fluorobenzene [(1] g, 8. 33 mmol) and dimethyl 2- nitromalonate (1.34 g, 7.58 mmol) were dissolved in mesitylene (10 ml). The solution was heated at [150°C] for about 12 h. Mesitylene was removed in vacuo and the residue was recrystallized from ethanol. 1.22 g (73%) of methyl 5- (2-fluorophenyl) isoxazole- 3-carboxylate was yielded as a light brown solid,

Reference： [1]Current Patent Assignee: PFIZER INC - WO2004/18428, 2004, A1 Location in patent: Page 280

6
[ 215124-04-2 ]
[ 766-49-4 ]
ethyl 6-chloro-8-[(2-fluorophenyl)ethynyl]-2-(trifluoromethyl)-2H-chromene-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With copper(l) iodide; triethylamine;tetrakis(triphenylphosphine) palladium(0); In toluene; at 20℃;	[0749] To 0.502 g (1.161 mmole) of ETHYL-6-CHLORO-8-IODO-2- (TRIFLUOROMETHYL)-2H- chromene-3-carboxylate was added 67 mg (0.060 mmole) tetrakis (triphenylphosphine) palladium (0), 22 mg (0.116 mmole) copper (I) iodide, 10 mL degassed toluene, 0.484 mL (3.48 mmole) degassed TEA, and 0.199 mL (1.74 mmole) 2- fluorophenylacetylene. The mixture was stirred overnight at room temperature. The mixture was concd and the resulting oil was purified using reverse phase chromatography to afford 0.440 g (89%) of a crystalline solid : 1H NMR (CDC13/400 MHz) 1.35 (t, 3H, J= 6.8 Hz), 4.26-4. 38 (m, 2H), 5.83 (q, 1H, J= 6.8 Hz), 7.08-7. 15 (m, 2H), 7.18 (d, 1H J= 2. 4 Hz), 7. 31- 7.37 (m, 1H), 7.45 (d, 1H, J= 2.4 Hz), 7.49-7. 53 (m, 1H), 7.63 (s, 1H) ; (ES+) 425 (M+1, 100).

Reference： [1]Patent: WO2004/87686,2004,A2 .Location in patent: Page 350

7
[ 74534-15-9 ]
[ 766-49-4 ]
[ 942189-67-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 20 - 70℃; for 2h;	Triethylamine (0.2ml, 1.43mmol) was added to a suspension of 1-Chloro-2- iodo-4-nitro-benzene 69 (Step 1) (100mg, 0.354mrnol), 1-ethynyl-2-fluorobenzene (100mg, 0.832mmol), copper iodide (100mg, 0.525mmol),Pd(PPh3)2Cl2 (100mg, 0.142mmol) in dimethylformamide (2ml) at room temperature, then stirred at 700C for 2 hours. Reaction was cooled to room temperature and extracted with ether (50ml), washed with v/ater(20ml), dried (MgSO4), filtered and solvent evaporated yielding a residue which chromatographed on silica gel eluting with 20% v/v MeCI2/hexanes yielding title product 70 as pale yellow solid (80mg,82%).

Reference： [1]Patent: WO2007/70398,2007,A1 .Location in patent: Page/Page column 229

8
[ 1027729-52-7 ]
[ 766-49-4 ]
[ 1027725-18-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In ethyl acetate; at 20 - 70℃; for 20.0h;	Step 2(S)-5-[(2-fluorophenyl)ethynyl]-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamideA mixture of (S)-5-bromo-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide (105 mg, 0.31mmol) and 1 -ethynyl-2-fluorobenzene (75 mg, 0.62 mmol) in 2.0 mL EtOAc was degassed with argon at 70 0C. Upon cooling to room temperature the reaction mixture was treated with triethylamine (0.16 mL, 1.1 mmol), dichlorobis(triphenylphosphine)palladium(II) (22 mg, 0.031 mmol) and copper(I)iodide (2 mg, 0.012 mmol). The reaction was heated at 70 0C for 20 hours then partitioned between EtOAc and H2O. The EtOAc layer was washed with acetic acid solution, saturated NaHCtheta3, brine, dried with anhydrous Na2Stheta4 and concentrated. The dark film obtained was purified by chromatography (silica gel, hexane/EtOAc) to give the title compound as a tan foam (110 mg, 94%).

Reference： [1]Patent: WO2008/61236,2008,A2 .Location in patent: Page/Page column 60

9
[ 766-49-4 ]
[ 445-28-3 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 2973 - 2975
[2]Advanced Synthesis and Catalysis,2016,vol. 358,p. 500 - 505

10
[ 914942-88-4 ]
[ 766-49-4 ]
C₂₁H₂₂FN₅O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2646 - 2649

11
[ 766-49-4 ]
[ 105752-11-2 ]
[ 1248699-41-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide; at 70℃; for 1h;	Step 1: 4-[(2-fluorophenyl)ethvnyl]pyridin-3-amineTo a solution of <strong>[105752-11-2]3-amino-4-iodopyridine</strong> in Dioxane/DMF (1 :1, 0.7M) were sequentially added NEt3 (5eq.), CuI (0.04 eq.), trans-bis(triphenylphosphine) palladium(II) chloride (0.02 eq.) and l-ethynyl-2-fluorobenzene (2 eq.). After heating for 1 h at 70 0C, water was added and the mixture was extracted with Et2O. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel, eluting with PE/EtOAc (50:50), affording the title compound(80%) as a solid. 1H NMR (400 MHz, OMSO-d6 + TFA, 300K) delta, 7.26-7.33 (dd, 2H, J = 7.6 Hz, J= 8 Hz), 7.52-7.53 (m, IH), 7.78 (d, IH, J= 8 Hz), 7.83 (t, IH, J= 6.4 Hz), 7.7 (d, IH, J= 5.6 Hz), 8.21 (s, IH); MS (ES+) m/z 213 (M +H)+.

Reference： [1]Patent: WO2010/115901,2010,A1 .Location in patent: Page/Page column 14

12
[ 766-49-4 ]
[ 1246224-44-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; silver nitrate; In acetone; at 20℃; for 3.0h;	General procedure: To the mixture of terminal alkyne (1 mmol), NBS (1.2 mmol) and 10 mL acetone, AgNO3 (5 mol %) was added and the mixture was stirred at room temperature for three hours. After the reaction completion, the solvent was evaporated and extracted with 10 mL petroleum ether (30-60C), then evaporated the solvent and the residue was the title product.
	With N-Bromosuccinimide; silver nitrate; In acetone; at 20℃; for 2.0h;Inert atmosphere;	General procedure: To a solution of substituted phenylacetylenes (S1) (20.0 mmol) in acetone (60 mL) was added NBS (4.22 g, 24.0 mmol) and AgNO3 (169.9 mg, 1.0 mmol), the resulting mixture was stirred under Ar at room temperature for 2 hours. After removing excess acetone, the reaction was quenched with saturated NH4Cl solution. The organic layer was extracted with petroleum ether (40 mL * 2), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford bromoalkynes S2.

Reference： [1]Journal of Catalysis,2017,vol. 353,p. 199 - 204
[2]Organic Letters,2019,vol. 21,p. 1569 - 1573
[3]Chemical Communications,2010,vol. 46,p. 8049 - 8051
[4]Tetrahedron Letters,2011,vol. 52,p. 5956 - 5959
[5]Chemical Communications,2012,vol. 48,p. 3545 - 3547
[6]Journal of Organic Chemistry,2015,vol. 80,p. 7519 - 7529
[7]Journal of the American Chemical Society,2017,vol. 139,p. 10302 - 10311
[8]Angewandte Chemie - International Edition,2019,vol. 58,p. 3589 - 3593
Angew. Chem.,2019,vol. 131,p. 3627 - 3631,5
[9]Organic Letters,2019,vol. 21,p. 3514 - 3517
[10]Chinese Chemical Letters,2020,vol. 31,p. 1564 - 1567

13
[ 1253373-80-6 ]
[ 766-49-4 ]
[ 1253373-81-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-ethyl-N,N-diisopropylamine;copper(l) iodide; In toluene; at 45℃; for 22.0h;	Compound 9 (8.80 mg, 16.7 mumol), 1 -ethynyl-2-fluorobenzene (5.67 mul_, 50.0 mumol), CuI (0.634 mg, 5.00 mumol) and DIPEA (8.55 mul_, 50.0 mumol) was dissolved in toluene (1 ml_). The mixture was heated to 45C and left to react for 22 h when it was diluted (CH2CI2), washed (HCI(aq) 5%, brine), dried (MgSO4), filtered and concentrated. Purification was made by flash chromatography using EtOAc:n-heptan (3:2) as eluent. The reaction yielded 93% of 10.

Reference： [1]Patent: WO2010/126435,2010,A1 .Location in patent: Page/Page column 20; 21; 28

14
[ 124-38-9 ]
[ 766-49-4 ]
[ 704-97-2 ]

Yield	Reaction Conditions	Operation in experiment
97%		General procedure: The terminal alkyne (1.0 mmol) was added to a mixtureof HSi(OEt)2Me (5.0 mmol) and KOtBu (1.5 mmol) in a10 mL Schlenk tube with a magnetic stirrer. The Schlenktube was evacuated and back-filled with CO2 for 3 times.After a CO2 ballon was connected, the reactor was moved toa water bath of 40 C. After being stirred for 2 h, the reactionmixture was diluted with water (30 mL), and was extractedwith CH2Cl2 (3×10 mL). The aqueous layer was acidifiedwith aqueous HCl (6 M) and then extracted with diethylether (5×20 mL). The combined organic extracts were driedover Na2SO4 and concentrated under vacuum to give the purepropiolic acid (such as compound 3-phenylpropiolic acid(3a): 98%).
94%		Sequentially adding a catalyst in the reaction bottle (14.0 mg, 0.025 millimole, 5mol %), cesium carbonate (32.6 mg, 1.0 mmol), 2-fluoro phenylacetylene (58 micro-liter, 0.5 mmol),N,N-dimethylformamide(3 ml), into the carbon dioxide, in the 40 C, reaction under normal pressure 16 hours. Reaction cooling to room temperature, diluted with water, acidified with hydrochloric acid, diethyl ether extraction, washing with saturated sodium chloride for ether level, dry anhydrous sodium sulfate, obtained product is vacuum to remove the solvent, the yield is 94%.
92%	With C76H124N6Nd2O6Si4; caesium carbonate; In dimethyl sulfoxide; at 40℃; under 760.051 Torr; for 24.0h;Inert atmosphere;	Under anhydrous anaerobic, under argon protection, 0.0622 g (3.85 x 10-5 mol) of {LNd [N (SiMe3) 2] · THF} 2 was added to the reaction flask, further, 0.6254 g (1.92 x 10-3 moles) of cesium carbonate was added. Under the protection of carbon dioxide bags, 2 ml of dimethyl sulfoxide was added, then 0.109 ml (9.62 x 10-4 mol) of 2-fluorophenyl acetylene was added, Then 3 ml of dimethylsulfoxide was added. The reaction was stirred in a constant temperature bath at 40 C. After 24 hours, the reaction was quenched by adding 10 mL of water, and then filtered. The clear solution was placed in a separatory funnel, a certain amount of hydrochloric acid solution was added to acidify, and extracted four times with ether. The extract was washed twice with saturated brine, liquid separation was carried out, the solvent was spin-dried, and then residual solvent was removed by pumping to obtain the product. The calculated yield was 92%.

82%

Table 5. Copper catalyzed carboxylation of terminal alkynes with CCv Reaction conditions: for LI, CuCl (2.0 mol %), TMEDA, 1.5 mol %; for L12, P(NHC)(NHC-Cu), 5 mol%; alkynes (2.0 mmol), base (2.4 mmol), C02 (1 atm), DMF (4 mL), r.t.. M monocarboxylic acid was obtained. General Procedure for Carboxylation of the Terminal Alkynes (lb as Example); CuCl (4.0 mg, 0.04 mmol, 2.0 mol %), TMEDA (3.5 mg, 0.03 mmol, 1.5 mol %), and K2C03 or Cs2C03 (2.4 mmol) were added to the DMF (4 mL) in the reaction tube (10 mL). C02 and 2 mmol of terminal alkynes (la, 204 mg) were introduced into the reaction mixture under stirring. The reaction mixture was stirred at room temperature (about 24 C) for 16 hours. After completion of the reaction, the reaction mixture was transferred to the potassium carbonate solution (2 N, 5 mL) and the mixture was stirred for 30 mins. The mixture was extracted with dichloromethane (3 >< 5 mL) and the aqueous layer was acidified with concentrated HC1 to PH = 1 , then extracted with diethyl ether (3 chi 5 mL) again. The combined organic layers were dried with anhydrous Na2S04, filtered and the solution was concentrated in vacuum affording pure product. Element analysis calcd (%) for lb [C9H602 (146.0)]: C 73.97, H 4.14; found: C 73.82, H 4.07. Data for 1H and 13C NMR of acids were all conducted in d - DMSO or CDC13 and consistent with the data in reported literatures.

Reference： [1]Science China Chemistry,2018,vol. 61,p. 449 - 456
[2]Patent: CN105585473,2016,A .Location in patent: Paragraph 0036; 0037
[3]Green Chemistry,2015,vol. 17,p. 1675 - 1682
[4]Patent: CN104177388,2016,B .Location in patent: Paragraph 0111; 0112
[5]New Journal of Chemistry,2017,vol. 41,p. 9250 - 9255
[6]Patent: WO2011/75087,2011,A1 .Location in patent: Page/Page column 17-18; 26
[7]ChemCatChem,2017,vol. 9,p. 882 - 887
[8]New Journal of Chemistry,2019,vol. 43,p. 10821 - 10825

15
diethyl ((3R,5R)-5-azido-2-methylisoxazolidin-3-yl)phosphonate [ No CAS ]
[ 766-49-4 ]
diethyl rac-(3R,5R)-5-(4-(2-fluorophenyl)-1H-1,2,3-triazol-1-yl)-2-methylisoxazolidin-3-yl-3-phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With copper(II) sulfate tetrahydrate; sodium L-ascorbate; In water; tert-butyl alcohol; at 20℃; for 48.0h;	General procedure: To a solution of the azidoisoxazolidine 12 or 13 (1.00 mmol) in tert-butanol (0.5 mL), CuSO4·4H2O (0.10 mmol) in water (1 mL) was added followed by sodium ascorbate (0.20 mmol) and the respective alkyne 14 (1.00 mmol). The reaction mixture was stirred at room temperature for 48 h, concentrated and co-evaporated with ethanol (3 × 10 mL). The residue was dissolved in chloroform (10 mL), dried over MgSO4, filtered through a pad of Celite and the solution was evaporated under reduced pressure. The crude product was purified on a silica gel column with chloroform:methanol (from 100:1 to 20:1, v/v) as eluent.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 501 - 509

16
[ 766-49-4 ]
[ 60509-38-8 ]
[ 563-96-2 ]
N-(2-bromobenzyl)-N-butyl-1,5-bis(2-fluorophenyl)pent-1-en-4-yn-3-amine [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1942 - 1945

17
[ 766-49-4 ]
[ 103-67-3 ]
[ 563-96-2 ]
N-benzyl-1,5-bis(2-fluorophenyl)-N-methylpent-1-en-4-yn-3-amine [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1942 - 1945

18
[ 766-49-4 ]
[ 74-88-4 ]
[ 1374672-84-0 ]

Yield	Reaction Conditions	Operation in experiment
24%	With sodium azide;copper(l) iodide; In water; acetonitrile; at 150℃; under 5171.62 Torr;	Example 8 4-(2-Fluorophenyl)-l-methyl-5-(l-(4-(trifluoromethyl)phenyl)-lH-imidazol-4-yl)-lH-l,2,3- triazole a) 4-(2-Fluorophenyl)- 1-methyl- 1H- 1 ,2,3-triazoleSolution A was composed of l-ethynyl-2-fluorobenzene (4.2 g, 35 mmol) and iodomethane (5.96 g, 42 mmol) in acetonitrile (94 mL) and Solution B was composed of sodium azide (2.73 g, 42 mmol) and copper(I) iodide (1.33 g, 6.99 mmol) in water (100 mL). The reaction was ran in Uniqsis FlowSyn apparatus at 150 C at 100 psi with flow rate of 1.0 mL/min and residence time of 1.5 min for each solution A and B. The reaction flow eluent was collected in an aqueous ammonium hydroxide solution (25%) and the mixture extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 10 to 60% ethyl acetate in heptane) afforded the title compound (1.5 g, 24%) as a light yellow solid. MS: m/e = 178.3 [M+H]+.
24%		Solution A was composed of <strong>[766-49-4]1-ethynyl-2-fluorobenzene</strong> (4.2 g, 35 mmol) and iodomethane (5.96 g, 42 mmol) in acetonitrile (94 mL) and Solution B was composed of sodium azide (2.73 g, 42 mmol) and copper(I) iodide (1.33 g, 6.99 mmol) in water (100 mL). The reaction was ran in Uniqsis FlowSyn apparatus at 150 C. at 100 psi with flow rate of 1.0 mL/min and residence time of 1.5 min for each solution A and B. The reaction flow eluent was collected in an aqueous ammonium hydroxide solution (25%) and the mixture extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 10 to 60% ethyl acetate in heptane) afforded the title compound (1.5 g, 24%) as a light yellow solid. MS: m/e=178.3 [M+H]+.

Reference： [1]Inorganic Chemistry,2017,vol. 56,p. 1616 - 1625
[2]Patent: WO2012/76590,2012,A1 .Location in patent: Page/Page column 28
[3]Patent: US2012/149675,2012,A1 .Location in patent: Page/Page column 12

19
[ 766-49-4 ]
[ 50919-06-7 ]

Reference： [1]Nature Chemistry,2014,vol. 6,p. 22 - 27
[2]Journal of the American Chemical Society,2012,vol. 134,p. 17376 - 17379,4
[3]Journal of the American Chemical Society,2014,vol. 136,p. 7058 - 7067

20
[ 766-49-4 ]
[ 445-26-1 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 17376 - 17379,4
[2]Organic Letters,2018,vol. 20,p. 1110 - 1113

21
[ 1035219-96-5 ]
[ 766-49-4 ]
[ 1446715-65-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4037 - 4043

22
[ 766-49-4 ]
[ 73183-34-3 ]
[ 633327-38-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With copper(l) iodide; N-cyclohexyl-cyclohexanamine; In water; at 45℃; for 20.0h;Inert atmosphere;	General procedure: CuI (10mol%), 1 (1 equiv, 0.5mmol), and 2 (2 equiv, 1.0mmol) were sequentially added under air to a dram vial equipped with a stir bar. Amine (1.5 equiv, 0.75mmol), and distilled water (1.0mL) were added by syringe, and the resulting mixture was vigorously stirred under nitrogen atmosphere [charged by general N2 (99.95%) gas flow] for 20hat the temperature, as shown in the tables. After this time, the contents of the flask were extracted with ethyl acetate and then concentrated by rotary evaporation. The residue was purified by flash chromatography, eluting with hexane/EtOAc to afford the product 3.

Reference： [1]Chemical Communications,2014,vol. 50,p. 2058 - 2060
[2]Tetrahedron,2017,vol. 73,p. 3999 - 4003

23
[ 349117-88-0 ]
[ 766-49-4 ]
[ 1556098-15-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With piperidine; bis-triphenylphosphine-palladium(II) chloride at 70℃; for 0.5h; Sealed tube;

Reference： [1]Brady, Ryan M.; Vom, Amelia; Roy, Michael J.; Toovey, Nathan; Smith, Brian J.; Moss, Rebecca M.; Hatzis, Effie; Huang, David C. S.; Parisot, John P.; Yang, Hong; Street, Ian P.; Colman, Peter M.; Czabotar, Peter E.; Baell, Jonathan B.; Lessene, Guillaume [Journal of Medicinal Chemistry, 2014, vol. 57, # 4, p. 1323 - 1343]

24
[ 766-49-4 ]
[ 50919-06-7 ]
[ 75321-85-6 ]

Reference： [1]Nature Chemistry,2014,vol. 6,p. 22 - 27

25
[ 766-49-4 ]
[ 75321-85-6 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 7892 - 7895
Angew. Chem.,2014,vol. 126,p. 8026 - 8029,4

26
[ 319474-34-5 ]
[ 766-49-4 ]
[ 1621927-91-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In 1,2-dimethoxyethane; at 80℃; for 2.83333h;Inert atmosphere; Sealed tube;	Step 2: In a microwave tube were placed 4-iodo-1 H-pyrrolo[2,3-b]pyridine (100 mg, 0.41 mmol), 1-ethynyl-2-fluorobenzene (93 , 0.82 mmol), tetrakis(triphenylphosphine)palladium(0) (5.8 mg, 0.01 mmol), copper (I) iodide (3.1 mg, 0.02 mmol), triethylamine (288 mu, 2.05 mmol), and dry 1 ,2-dimethoxyethane (2.00 mL). The tube was sealed and nitrogen gas was bubbled in the reaction mixture for 10 min. The reaction mixture was heated at 80 C for 2h. The reaction mixture was cooled down, diluted with a saturated solution of sodium bicarbonate and extracted with ethyl acetate. The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was purified by chromatography using hexane / ethyl acetate (20% to 100%) as eluent to give title compound 4-(2-fluoro-phenylethynyl)-1H-pyrrolo[2,3-b]pyridine (81 mg; 82%) as a tan solid; LCMS (ESI) 237 (M+H); HPLC 98.4%, RT: 4.60 min; H NMR (500 MHz, DMSO-c6) delta ppm: 11.95 (s, 1H), 8.26 (d, J=4.9, 1H), 7.75 (td, J=7.5, 1.6, 1H), 7.63 (dd, J=3.1, 2.7, 1H), 7.59-7.51 (m, 1H), 7.40 (t, J=9.1, 1H), 7.32 (td, J=7.6, 0.9, 1H), 7.23 (d, J=4.9, 1H), 6.60 (dd, J=3.3, 1.9, 1H).

Reference： [1]Patent: WO2014/121883,2014,A1 .Location in patent: Page/Page column 54-55

27
[ 696-62-8 ]
[ 766-49-4 ]
[ 1007120-38-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	With C17H32Cl2N4OPd; potassium carbonate; In ethanol; at 80℃; for 1.0h;	General procedure: K2CO3 (2.5 × 10-4 mol, 2.5 equiv), aryl iodide (1.0 × 10-4 mol, 1.0 equiv), and alkyne (1.5 × 10-4 mol, 1.5 equiv) were mixed in a 10-mL vial, followed by addition of a solution of the selected catalyst (1 × 10-8 mol) in EtOH (1 mL). The vial was placed in a preheated oil bath at 80 C and stirred for 1 h. After cooling to 20-25 C, the reaction mixture was evaporated to dryness under a stream of dinitrogen followed by addition of 1.0 equiv of 1,2-dimethoxyethane as NMR internal standard, and extraction of the reaction mixture with three 0.20-mL portions of CDCl3. All fractions were joined and analyzed by 1H NMR spectroscopy. The product peak assignments were based on the authentic samples or on published dat, whereas quantifications were performed upon integration of the selected peak of the product relatively to the peak of the standard.
	With C23H20Cl4N4OPd; potassium carbonate; In ethanol; at 80℃; for 4.0h;	General procedure: Selected base (1.5×10-4 mol, 1.5 equivs), aryl iodide (1.0×10-4 mol, 1.0 equiv) and terminal alkyne (1.0×10-4 mol, 1.0 equivs) were mixed in a 10-mL vial, followed by addition of a solution of the selected catalyst (1×10-8 mol) in EtOH (1 mL). The vial was placed in a pre heated oil bath at 80 C and stirred for 4 h. After cooling to ca. 25 C, the reaction mixture was evaporated to dryness under a stream of dinitrogen followed by addition of 1.0 equivof 1,2-dimethoxyethane (NMR internal standard), and extraction of the reaction mixture with three 0.20 mL portions of CDCl3. All fractions were joined and analyzed by 1H NMR spectroscopy. The product peak assignments were based on authentic samplesor on published data [56,62-68] (several sources were used for published compounds), while the structure of two new products,i.e. 3,4-dimethoxy-5-(phenylethynyl)benzaldehyde (derived from the coupling of 3-iodo-4,5-dimethoxybenzaldehyde with phenylacetylene) and 1-fluoro-2-[(2-methylphenyl)ethynyl]benzene (prepared from 2-fluorophenylacetylene and 2-iodotoluene were undoubtedly established using NMR spectroscopy, MS and elemental analyses (see Supplementary data). Quantifications were performed upon integration of the selected peak of the product in the 1H NMR relatively to the peak of the standard.

Reference： [1]Journal of Catalysis,2015,vol. 329,p. 449 - 456
[2]Journal of Molecular Catalysis A: Chemical,2014,vol. 395,p. 162 - 171

28
[ 615-37-2 ]
[ 766-49-4 ]
1-fluoro-2-[(2-methylphenyl)ethynyl]benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With C22H20Cl4N4O2PdS; potassium carbonate; In ethanol; at 80℃; for 1.0h;	General procedure: K2CO3 (2.5 × 10-4 mol, 2.5 equiv), aryl iodide (1.0 × 10-4 mol, 1.0 equiv), and alkyne (1.5 × 10-4 mol, 1.5 equiv) were mixed in a 10-mL vial, followed by addition of a solution of the selected catalyst (1 × 10-8 mol) in EtOH (1 mL). The vial was placed in a preheated oil bath at 80 C and stirred for 1 h. After cooling to 20-25 C, the reaction mixture was evaporated to dryness under a stream of dinitrogen followed by addition of 1.0 equiv of 1,2-dimethoxyethane as NMR internal standard, and extraction of the reaction mixture with three 0.20-mL portions of CDCl3. All fractions were joined and analyzed by 1H NMR spectroscopy. The product peak assignments were based on the authentic samples or on published dat, whereas quantifications were performed upon integration of the selected peak of the product relatively to the peak of the standard.
	With C33H34Cl2N4O2Pd; potassium carbonate; In ethanol; at 80℃; for 4.0h;	General procedure: Selected base (1.5×10-4 mol, 1.5 equivs), aryl iodide (1.0×10-4 mol, 1.0 equiv) and terminal alkyne (1.0×10-4 mol, 1.0 equivs) were mixed in a 10-mL vial, followed by addition of a solution of the selected catalyst (1×10-8 mol) in EtOH (1 mL). The vial was placed in a pre heated oil bath at 80 C and stirred for 4 h. After cooling to ca. 25 C, the reaction mixture was evaporated to dryness under a stream of dinitrogen followed by addition of 1.0 equivof 1,2-dimethoxyethane (NMR internal standard), and extraction of the reaction mixture with three 0.20 mL portions of CDCl3. All fractions were joined and analyzed by 1H NMR spectroscopy. The product peak assignments were based on authentic samplesor on published data [56,62-68] (several sources were used for published compounds), while the structure of two new products,i.e. 3,4-dimethoxy-5-(phenylethynyl)benzaldehyde (derived from the coupling of 3-iodo-4,5-dimethoxybenzaldehyde with phenylacetylene) and 1-fluoro-2-[(2-methylphenyl)ethynyl]benzene (prepared from 2-fluorophenylacetylene and 2-iodotoluene were undoubtedly established using NMR spectroscopy, MS and elemental analyses (see Supplementary data). Quantifications were performed upon integration of the selected peak of the product in the 1H NMR relatively to the peak of the standard.

Reference： [1]Journal of Catalysis,2015,vol. 329,p. 449 - 456
[2]Journal of Molecular Catalysis A: Chemical,2014,vol. 395,p. 162 - 171

29
[ 2564-83-2 ]
[ 766-49-4 ]
(E)-1-((1-(2-fluorophenyl)-2-nitrovinyl)oxy)-2,2,6,6-tetramethylpiperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tert.-butylnitrite In tetrahydrofuran at 70℃; for 24h; stereoselective reaction;

Reference： [1]Yan, Hong; Rong, Guangwei; Liu, Defu; Zheng, Yang; Chen, Jie; Mao, Jincheng [Organic Letters, 2014, vol. 16, # 24, p. 6306 - 6309]

30
[ 650600-16-1 ]
[ 766-49-4 ]
[ 1008-75-9 ]
[ 1616956-25-2 ]
4-(2-fluorophenylethynyl)-3-methyl-5-phenylisoxazole [ No CAS ]
1,1′-buta-1,3-diyne-1,4-diylbis(2-fluorobenzene) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 36% 2: 19% 3: 5% 4: 26%	With potassium phosphate; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); Selectfluor In water; acetonitrile at 20℃; for 20h; Inert atmosphere;	Synthesis of 4-(2-Fluorophenylethynyl)-3-methyl-5-phenylisoxazole (4g) General procedure: To a stirring solutionof K3PO4 (170 mg, 800 μmol), PPh3AuNTf2 (29.6 mg, 40.0 μmol) and Selectfluor (354 mg, 1.00 mmol) in MeCN (4 mL) were added (Z)-4-phenylbut-3-yn-2-one O-methyloxime (1a) (69.3 mg, 400 μmol), phenylacetylene (3a) (88.0μL, 800 μmol) and H2O (72.0 μL) sequentially under Ar atmosphere. The resulting suspension was stirred at rt for 17h. After the completion of the reaction, the reaction mixture was diluted with H2O (20 mL) and extracted with EtOAc (3× 20 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and evaporated. Purification by column chromatography (35:1 hexane/EtOAc) afforded 4a (52 mg, 50%) as a yellow solid, 5 (12.6 mg, 20%) as ayellow solid, 6 (12.9 mg, 18%) as a yellow liquid, and 7a (43.6 mg, 27%) as a white solid.

Reference： [1]Song, Doo-Hee; Ryu, Jae-Sang [Bulletin of the Korean Chemical Society, 2014, vol. 35, # 9, p. 2635 - 2644]

31
[ 32024-15-0 ]
[ 766-49-4 ]
C₁₇H₁₃FO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With C19H28Cl2N4O2Pd; potassium carbonate; In ethanol; at 80℃; for 1h;	General procedure: K2CO3 (2.5 × 10-4 mol, 2.5 equiv), aryl iodide (1.0 × 10-4 mol, 1.0 equiv), and alkyne (1.5 × 10-4 mol, 1.5 equiv) were mixed in a 10-mL vial, followed by addition of a solution of the selected catalyst (1 × 10-8 mol) in EtOH (1 mL). The vial was placed in a preheated oil bath at 80 C and stirred for 1 h. After cooling to 20-25 C, the reaction mixture was evaporated to dryness under a stream of dinitrogen followed by addition of 1.0 equiv of 1,2-dimethoxyethane as NMR internal standard, and extraction of the reaction mixture with three 0.20-mL portions of CDCl3. All fractions were joined and analyzed by 1H NMR spectroscopy. The product peak assignments were based on the authentic samples or on published dat, whereas quantifications were performed upon integration of the selected peak of the product relatively to the peak of the standard.

Reference： [1]Journal of Catalysis,2015,vol. 329,p. 449 - 456

32
[ 4556-23-4 ]
[ 766-49-4 ]
4-((1-(2-fluorophenyl)vinyl)thio)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With palladium diacetate; copper(II) bis(trifluoromethanesulfonate) In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 4h; Inert atmosphere;	Typical procedure for the preparation of 2-((1-phenylvinyl)thio)pyridine (3a) General procedure: A test tube was charged with pyridine-2-thiol (0.2 mmol), Pd(OAc)2 (0.004 mmol), Cu(OTf)2 (0.01 mmol), phenylacetylene (0.24 mmol), in xylene (1 mL). The reaction tube was evacuated and back-filled with N2 (3 times, balloon). Then the reaction mixture was stirred at 120°C (oil bath temperature) under N2 balloon for 4 h. After cooling to room temperature, the solvent was extracted with ethyl acetate and washed with brine. After the solvent was evaporated in vacuo, the residues were purified by column chromatography, eluting with petroleum ether/EtOAc to afford pure 2-((1-phenylvinyl)thio)pyridine.

Reference： [1]Ma, Haojie; Ren, Xiaoyu; Zhou, Xiaoqiang; Ma, Chaowei; He, Yongqin; Huang, Guosheng [Tetrahedron Letters, 2015, vol. 56, # 44, p. 6022 - 6029]

33
[ 766-49-4 ]
[ 98-86-2 ]
[ 58549-53-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12.0h;Inert atmosphere;	In the reaction flask, 0.25 mmol of o-fluorophenylacetylene was added,0.25 mmol of acetophenone, 0.25 mmol of potassium tert-butoxide and 1 ml of dimethylsulfoxide were added and stirred under a nitrogen gas atmosphere at 120C for 12 hours. The heating and stirring were stopped, and the mixture was cooled to room temperature. The crude product was distilled under reduced pressure and purified by column chromatography to obtain the desired product. The eluant used in the column chromatography was pure hexane, and the yield was 92%.

Reference： [1]Patent: CN104650025,2016,B .Location in patent: Paragraph 0105; 0106; 0107; 0108; 0109; 0110; 0111-0114
[2]Journal of Organic Chemistry,2016,vol. 81,p. 912 - 919

34
[ 766-49-4 ]
[ 2124-31-4 ]
4-(benzo[b]oxepin-2-yl)-N,N-dimethylaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12.0h;Inert atmosphere;	In the reaction flask, 0.25 mmol of o-fluorophenylacetylene was added,0.25 mmol of 4-dimethylacetophenone, 0.25 mmol of potassium tert-butoxide and 1 ml of dimethylsulfoxide were added and stirred under a nitrogen gas atmosphere at 120C for 12 hours. The heating and stirring were stopped, and the mixture was cooled to room temperature. The crude product was distilled under reduced pressure and purified by column chromatography to obtain the desired product. The eluant used in the column chromatography was pure hexane, and the yield was 91%.

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 912 - 919
[2]Patent: CN104650025,2016,B .Location in patent: Paragraph 0115; 0116; 0117; 0118; 0119; 0120; 0121-0124

35
[ 347-84-2 ]
[ 766-49-4 ]
2-(4-fluorophenyl)-3-phenylbenzo[b]oxepine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 912 - 919

36
[ 766-49-4 ]
[ 1889-71-0 ]
2-(4-chlorophenyl)-3-phenylbenzo[b]oxepine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 912 - 919

37
[ 1023-17-2 ]
[ 766-49-4 ]
2-(4-methoxyphenyl)-3-phenylbenzo[b]oxepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12.0h;Inert atmosphere;	In the reaction flask, 0.25 mmol of o-fluorophenylacetylene was added,0.25 mmol of 1-(4-methoxyphenyl)-2-phenylethanone, 0.25 mmol of potassium tert-butoxide and 1 ml of dimethylsulfoxide were added and stirred under a nitrogen gas atmosphere at 120C for 12 hours. The heating and stirring were stopped, and the mixture was cooled to room temperature. The crude product was distilled under reduced pressure and purified by column chromatography to obtain the desired product. The eluant used in the column chromatography was pure hexane, and the yield was 72%.

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 912 - 919
[2]Patent: CN104650025,2016,B .Location in patent: Paragraph 0135; 0136; 0137; 0138; 0139; 0140; 0141-0144

38
[ 766-49-4 ]
[ 5586-88-9 ]
3-(4-chlorophenyl)-2-methylbenzo[b]oxepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12.0h;Inert atmosphere;	To the reaction flask was added 0.25 mmol of o-fluorophenylacetylene,0.25 mmol of 1- (4-chlorophenyl) -2-propanone,0.25 mmol of potassium tert-butoxide,1 ml of dimethylsulfoxide,Under N2 gas protection,After stirring for 12 hours at 120 C, heating and stirring were stopped, and the mixture was cooled to room temperature. The crude product was distilled under reduced pressure and purified by column chromatography.To obtain the target product, the column chromatography eluent used is pure hexane,Yield 85%.

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 912 - 919
[2]Patent: CN104650025,2016,B .Location in patent: Paragraph 0065; 0066; 0067; 0068; 0069; 0070; 0071-0074

39
[ 122-84-9 ]
[ 766-49-4 ]
3-(4-methoxyphenyl)-2-methylbenzo[b]oxepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12.0h;Inert atmosphere;	In the reaction flask, 0.25 mmol of o-fluorophenylacetylene was added,0.25 mmol of 1- (4-methoxyphenyl) -2-propanone, 0.25 mmol of potassium tert-butoxide and 1 ml of dimethylsulfoxide were added and stirred under a nitrogen gas atmosphere at 120 C for 12 hours. The heating and stirring were stopped, and the mixture was cooled to room temperature. The crude product was distilled under reduced pressure and purified by column chromatography to obtain the desired product. The eluant used in the column chromatography was pure hexane, and the yield was 83%.

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 912 - 919
[2]Patent: CN104650025,2016,B .Location in patent: Paragraph 0075; 0076; 0077; 0078; 0079; 0080; 0081-0084

40
[ 3027-13-2 ]
[ 766-49-4 ]
3-(3-methoxyphenyl)-2-methylbenzo[b]oxepine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 912 - 919

41
[ 5211-62-1 ]
[ 766-49-4 ]
3-(2-methoxyphenyl)-2-methylbenzo[b]oxepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 120℃; for 12h; Schlenk technique; Inert atmosphere;

Reference： [1]Ouyang, Lu; Qi, Chaorong; He, Haitao; Peng, Youbin; Xiong, Wenfang; Ren, Yanwei; Jiang, Huanfeng [Journal of Organic Chemistry, 2016, vol. 81, # 3, p. 912 - 919]

42
[ 2893-05-2 ]
[ 766-49-4 ]
2-isopropyl-3-phenylbenzo[b]oxepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 120℃; for 12h; Schlenk technique; Inert atmosphere;

Reference： [1]Ouyang, Lu; Qi, Chaorong; He, Haitao; Peng, Youbin; Xiong, Wenfang; Ren, Yanwei; Jiang, Huanfeng [Journal of Organic Chemistry, 2016, vol. 81, # 3, p. 912 - 919]

43
[ 25870-62-6 ]
[ 766-49-4 ]
2-butyl-3-phenylbenzo[b]oxepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12.0h;Inert atmosphere;	In the reaction flask, 0.25 mmol of o-fluorophenylacetylene was added,0.25 mmol of 1-phenyl-2-hexanone, 0.25 mmol of potassium tert-butoxide and 1 ml of dimethylsulfoxide were added and stirred under a nitrogen gas atmosphere at 120 C for 12 hours. The heating and stirring were stopped, and the mixture was cooled to room temperature. The crude product was distilled under reduced pressure and purified by column chromatography to obtain the desired product. The eluant used in the column chromatography was pure hexane, and the yield was 80%

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 912 - 919
[2]Patent: CN104650025,2016,B .Location in patent: Paragraph 0085; 0086; 0087; 0088; 0089; 0090; 0091-0094

44
[ 766-49-4 ]
[ 102-04-5 ]
2-benzyl-3-phenylbenzo[b]oxepine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 912 - 919
[2]Patent: CN104650025,2016,B .Location in patent: Paragraph 0095; 0096; 0097; 0098; 0099; 0100; 0101-0104

45
[ 6302-02-9 ]
[ 766-49-4 ]
2-(2-methylbenzo[b]oxepin-3-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12h;Inert atmosphere;	In the reaction flask, 0.25 mmol of o-fluorophenylacetylene was added,0.25 mmol of 1- (2-pyridyl) -2-propanone, 0.25 mmol of potassium tert-butoxide and 1 ml of dimethylsulfoxide were added and stirred under a nitrogen gas atmosphere at 120C for 12 hours. The heating and stirring were stopped, and the mixture was cooled to room temperature. The crude product was distilled under reduced pressure and purified by column chromatography to obtain the desired product. The eluant used in the column chromatography was pure hexane, and the yield was 72%.

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 912 - 919
[2]Patent: CN104650025,2016,B .Location in patent: Paragraph 0145; 0146; 0147; 0148; 0149; 0150; 0151-0154

46
[ 766-49-4 ]
[ 108-94-1 ]
1,2,3,4-tetrahydrodibenzo[b,f]oxepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12.0h;Inert atmosphere;	In the reaction flask, 0.25 mmol of o-fluorophenylacetylene was added,0.25 mmol of cyclohexanone, 0.25 mmol of potassium tert-butoxide and 1 ml of dimethylsulfoxide were added and stirred under a nitrogen gas atmosphere at 120C for 12 hours. The heating and stirring were stopped, and the mixture was cooled to room temperature. The crude product was distilled under reduced pressure and purified by column chromatography to obtain the desired product. The eluant used in the column chromatography was pure hexane, and the yield was 78%.

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 912 - 919
[2]Patent: CN104650025,2016,B .Location in patent: Paragraph 0164; 0165; 0166; 0167; 0168; 0169; 0170-0173

47
[ 766-49-4 ]
[ 25015-63-8 ]
[ 633327-38-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride; tris-tert-butylphosphinimide, lithium salt; In benzene; at 20℃; for 13.0h;Glovebox; Inert atmosphere;	General procedure: In an N2 charged glove box with oxygen and water levels ?0.1 ppm, to an oven-dried screwed vial were added SIPrCuCl (c8) (4.9 mg, 5 mol%, 0.01 mmol), tri(t-Butyl)phosphoranimide (1b) (2.2 mg, 5 mol%, 0.01 mmol), Pinacolborane (1c) (28 mg, 0.22 mmol, 1.1 eq.), terminal alkyne (1) (0.2 mmol, 1 eq.) and benzene (2 mL, 0.1 M). The formed reaction mixture was kept stirring for 13-15 hours in glove box. Then the dark brown reaction mixture was taken out from glove box the solvent was removed by rotary evaporator. The solvent mixture (Hexane:Ethyl acetate) was added into the reaction residue as eluent then kept stirring for about 30 mins under room temperature until the precipitate was formed. The mixture was further filtered through a short pad of silica gel to get colorless filtrate. Organic solvents were removed under reduced pressure and desired product was obtained after dryness under vacuum without further purification.
76%	With Schwartz's reagent; triethylamine; at 50℃;	C.i. (E)-2-(2-Fluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane : To a mixture of 2-fluorophenyl acetylene (commercial, 2 g; 16.1 mmol) and TEA (0.23 mL, 1.65 mmol) were added pinacolborane (3.6 mL; 24.1 mmol) and Cp2ZrHCI (0.45 g; 1.65 mmol). The suspension was heated at 50C overnight. The reaction mixture was diluted with EA and filtered. The filtrate was concentrated to dryness and the evaporation residue was purified by CC (Hept.-EA gradient) to afford the title compound (3.06 g; 76% yield) as a yellow oil.1H NMR (DMSO-d6) delta: 7.77 (m, 1H); 7.38-7.44 (m, 2H); 7.22-7.26 (m, 2H); 6.25 (d, J = 18.6 Hz, 1H); 1.26 (s, 12H).

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 1523 - 1527
[2]Organic Letters,2019,vol. 21,p. 4035 - 4038
[3]Organic Letters,2017,vol. 19,p. 4323 - 4326
[4]Patent: WO2019/86452,2019,A1 .Location in patent: Page/Page column 41
[5]European Journal of Organic Chemistry,2020,vol. 2020,p. 3024 - 3029
[6]Journal of the American Chemical Society,2016,vol. 138,p. 2548 - 2551

48
[ 33775-94-9 ]
[ 766-49-4 ]
[ 936734-95-1 ]

Yield	Reaction Conditions	Operation in experiment
20%	With potassium hydroxide In dimethyl sulfoxide at 25℃; for 26h; Inert atmosphere; Sealed tube; Irradiation; regioselective reaction;

Reference： [1]Gao, Li; Chang, Bin; Qiu, Wenzhao; Wang, Lele; Fu, Xianzhi; Yuan, Rusheng [Advanced Synthesis and Catalysis, 2016, vol. 358, # 8, p. 1202 - 1207]

49
[ 766-49-4 ]
[ 445-27-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With silver trifluoromethanesulfonate; In water; acetic acid; at 110℃; for 6.0h;Schlenk technique;	General procedure: To a 25mL Schlenk tube, AuSBA-15 (6wt%, 20mg), AgOTf (0.05mmol) was added to a solution of phenylacetylene (1.0mmol) in HOAc/H2O (3.0mL, 15:1) under ambient air, the resulting mixture was stirred for 6hat 110C. It was monitored by TLC. After the reaction was completed, the solvent was removed under reduced pressure and purified of the crude product by column chromatography on silica-gel afforded the desired compound.
80%	With p-toluenesulfonic acid monohydrate; acetic acid; In dichloromethane; at 80℃; for 8.0h;Sealed tube;	General procedure: The corresponding alkyne (1 mmol) was added to a solution of p-toluenesulfonic acidmonohydrate (1 mmol, 0.190 g), acetic acid (0.5 mL) in CH2Cl2 (1.0 mL). Thereaction was then sealed and stirred at the indicated temperature (oC) and for theindicated amount of times (h) in Table 2. After completion, saturated aqueousNaHCO3 (10 mL) was added to quench the reaction and then extracted with CH2Cl2(10 mL×3). The organic layer was dried over Na2SO4 and concentrated in vacuo. Theresidue was purified by column chromatography to give the pure product. Forsubstrates 1j. 1l, 1n, 1p and 1q, DCE was used as solvent in consideration ofoperation convenience.
	With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water; silver trifluoromethanesulfonate; In methanol; at 120℃; for 6.0h;	The <strong>[766-49-4]1-ethynyl-2-fluorobenzene</strong> (120 mg, 1.0 mmol), cat. [Au] (6 mg, 1 muM %), AgOTf (2.6 mg, 1 muM %), water (36 mg, 2 mmol) and methanol (1 ml) are added to the 25 mL of Claisen tube or. After closing the reaction at 120 C for 6 hours, cooling to room temperature. Then adding formic acid amine (315 mg, 5 mmol) and cat. [Rh] (6.2 mg, 1 mmol %), the reaction mixture in oil bath heated to 80 C, reaction 12 hours, cooling to room temperature. Rotary evaporation of the solvent and add a certain amount of ethyl acetate and water extraction, the organic phase of the resulting product after concentrated hydrochloric acid the reflux process, rotary evaporation to remove the solvent, the final petroleum ether washing and filtering to obtain the pure target compound, yield: 81%

Reference： [1]Inorganic Chemistry Communications,2019,vol. 109
[2]Journal of Organometallic Chemistry,2017,vol. 851,p. 46 - 51
[3]Synlett,2016,vol. 27,p. 2378 - 2383
[4]Organic Letters,2018,vol. 20,p. 1110 - 1113
[5]RSC Advances,2018,vol. 8,p. 14829 - 14832
[6]Patent: CN109384677,2019,A .Location in patent: Paragraph 0099-0102

50
[ 119-80-2 ]
[ 766-49-4 ]
1-(2-fluorophenyl)-2-[(2-carboxyphenyl)thio]ethene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With potassium hydroxide In water for 48h; Heating; Green chemistry; stereoselective reaction;	General procedure for the phenylacetylene hydrothiolation with 2,2’-dithiosalicylic acid General procedure: A solution of DTSA (1.5mmol, 0.4595 g), phenylacetylene (2.0mmol, 0.22 mL), and 40% KOH aqueous solution (0.2 mL) in 2 mL H2O was heated at 130 °C for 48 h on an oil bath. The reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was cooled to room temperature naturally and extracted with 20 mL ethyl acetate and 2 mL saturated sodium chloride aqueous solution. The organic layer was separated, washed with a saturated NaCl solution thrice, and dried over anhydrous magnesium sulfate. The solvent was evaporated using arotary evaporator to afford the crude product. The crude product was purifiedby column chromatography as follows: First, PE with a boiling point range of 60-90 °C was used to wash the column. Then, the crude sample was loaded, and the column was eluted with amixture of PE/ethyl acetate (10:1, v/v). The eluate with an Rf value of 0.3 was collected, and the solvent was evaporated using a rotary evaporator to afford 1-phenyl-2-[2-carboxyphenyl)thio]ethene. The E/Z was determinedby 1H NMR spectroscopy.

Reference： [1]Ye, Yanyan; Huang, Chengcheng; Zhao, Caixia; Ren, Baodong; Xiao, Hongping; Li, Xinhua [Synthetic Communications, 2016, vol. 46, # 19, p. 1634 - 1641]

51
[ 713-45-1 ]
[ 766-49-4 ]
C₁₈H₁₃F₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12h;Inert atmosphere;	In the reaction flask, 0.25 mmol of o-fluorophenylacetylene was added,0.25 mmol of <strong>[713-45-1]1-(4-trifluoromethylphenyl)-2-propanone</strong>, 0.25 mmol of potassium tert-butoxide and 1 ml of dimethylsulfoxide were added and stirred under a nitrogen gas atmosphere at 120°C for 12 hours. The heating and stirring were stopped, and the mixture was cooled to room temperature. The crude product was distilled under reduced pressure and purified by column chromatography to obtain the desired product. The eluant used in the column chromatography was pure hexane, and the yield was 42percent.

Reference： [1]Patent: CN104650025,2016,B .Location in patent: Paragraph 0125; 0126; 0127; 0128; 0129; 0130; 0131-0134

52
[ 766-49-4 ]
[ 140-29-4 ]
(Z)-4-(2-fluorophenyl)-2-phenylbut-2-enenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium tert-butylate; In dimethyl sulfoxide; tert-butyl alcohol; at 80℃; for 12.0h;Inert atmosphere;	In the reaction flask was added 0.3 mmol of o-fluorophenyl acetylene, 0.3 mmol phenylacetonitrile, 0.3 mmol of potassium tert-butoxide, 0.3 mmol of tert-butyl alcohol, 1 ml of dimethylsulfoxide at 80 C with nitrogen after stirring for 12 hours under the protection of the heating and stirring is stopped, cooled to room temperature.The reaction was washed with 15mL water, then extracted three times with ethyl acetate (each with I OmL), combined organic layers were dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and then purified by column chromatography to give the desired product, column chromatography eluent used was a volume ratio of 100: 1 n-hexane and ethyl acetate mixed solvent, a yield of 83%.

Reference： [1]Patent: CN106116998,2016,A .Location in patent: Paragraph 0048
[2]Advanced Synthesis and Catalysis,2017,vol. 359,p. 1339 - 1350

53
[ 766-49-4 ]
[ 100-39-0 ]
[ 1263862-46-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With copper(l) iodide; sodium azide; diethylamine; In glycerol; at 20℃; for 3.0h;Schlenk technique; Inert atmosphere; Green chemistry;	General procedure: A mixture of alkynes (0.24 mmol), sodium azide (0.24 mmol), halides (0.20 mmol) were added and stirred in glycerol (1.0 ml) in the presence of CuI (0.002 mmol) and diethylamine (0.01 mmol) at room temperature in a schlenk under nitrogen. The progress of the reaction was monitored by HPLC until the reaction was complete. The mixture was added water (10 ml) and extracted with ethyl acetate (3*20 mL). The onganic layer was dried over anhydrous Na2SO4. Then the residue was subjected to flash column chromatography on silica gel (petroleum ether/ethyl acetate) to afford the corresponding compounds 4.

Reference： [1]Organometallics,2017,vol. 36,p. 2116 - 2125
[2]Synthesis,2018,vol. 50,p. 2191 - 2199

54
[ 766-49-4 ]
[ 25015-63-8 ]
2-[2-(2-fluorophenyl)vinyl]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With C39H65CuN3P; In benzene; at 20℃; for 13.0h;	The boron hydrogenation of o-fluorophenylacetylene was catalyzed by complex B to give product 2c in 99% yield.

Reference： [1]Patent: CN106243132,2016,A .Location in patent: Paragraph 0057; 0058
[2]Green Chemistry,2017,vol. 19,p. 4169 - 4175

55
[ 98-66-8 ]
[ 766-49-4 ]
1-(2-fluorophenyl)vinyl 4-chlorobenzenesulfonate [ No CAS ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 3530 - 3534

56
[ 766-49-4 ]
[ 1576-35-8 ]
(E)-1-fluoro-2-(1-iodo-2-tosylvinyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With dipotassium peroxodisulfate; tetra-(n-butyl)ammonium iodide; In acetonitrile; at 80℃; for 0.5h;Sealed tube; Green chemistry;	General procedure: Phenylacetylene 1a (0.051 g, 0.5 mmol), 4-methylbenzenesulfonyl hydrazide 2a (0.112 g, 0.6 mmol), TBAI (0.222 g, 0.6 mmol), and K2S2O8 (0.270 g, 1 mmol) were added to CH3CN (2 mL) in a sealed tube with magnetic stirring at 80 C (oil bath) for 30 min. After the completion of reaction (monitored by thin-layer chromatography (TLC)), the sealed tube was allowed to cool to room temperature. Then, the reaction solution was filtered and removed under vacuum, and the residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate 1:10) to give desired product 3aa.
66%	With potassium iodide; dibenzoyl peroxide; In dimethyl sulfoxide; at 20℃; for 12.0h;	General procedure: A 25 mL round-bottom ask was charged with alkynes 1 (0.2 mmol), sulfonylhydrazides 2 (0.3 mmol), KI(0.2 mmol), BPO (0.2 mmol, benzoyl peroxide), and DMSO(2 mL). Then the mixture was stirred at room temperature in air over night. Upon completion (TLC), the reaction mixture was mixed with water (10 mL), and the resulting suspension was extracted with ethyl acetate (3 × 10 mL). The combined organic phase was dried over anhydrous Na2SO4 and fltrated.The solution was evaporated under reduced pressure to remove the solvent. Purifcation of the residue by ash silica column chromatography using ethyl acetate (EA)/and petroleum ether(PET) mixtures as eluent (VEA: VPET = 1: 15) afforded pure product. NMR Spectra were measured in CDCl3 at 400 MHz (1H) and 100 MHz (13C). The Supplemental Materials file contains sample 1H and 13C NMR of the products 3 (FiguresS2-S33). (E)-1-(2-Iodo-2-phenylvinylsulfonyl)-4-methylbenzene(3a).17 White solid; m.p. 69 C; 1H NMR: delta 7.44 (d, J = 8.0 Hz,2 H), 7.36 (s, 1 H), 7.31-7.25 (m, 3 H), 7.22 (d, J = 6.0 Hz, 2 H),7.17 (d, J = 7.6 Hz, 2 H), 2.37 (s, 3 H); 13C NMR: 144.6, 141.3,139.7, 137.2, 129.8, 129.7, 127.95, 127.88, 127.7, 114.3, 21.7.

Reference： [1]Synthetic Communications,2017,vol. 47,p. 1927 - 1933
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2017,vol. 192,p. 1301 - 1304

57
[ 766-49-4 ]
4-(4-azidophenoxy)-N-methylpicolinamide [ No CAS ]
4-(4-(4-(2-fluorophenyl)-1H-1,2,3-triazol-1-yl)phenoxy)-N-methylpicolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium L-ascorbate; In methanol; at 25℃; for 16.0h;Inert atmosphere; Schlenk technique;	General procedure: Under N2 atmosphere, the mixture of alkyne (0.3 mmol), azide (0.3 mmol), Na ascorbate(0.006 mmol, 2 mol %), and 0.3 103 M solution of catalyst 2 in MeOH (0.1-0.3 mol %) was stirredin a 10 mL Schlenk tube at 25 C for 16 h. Evaporation of the solvents followed by purification byshort column chromatography on silica gel provided the desired 1,4-disubstituted triazole product.The unreacted alkyne and azide were rst eluted out with 3/1 petroleum ether (PE)/ethyl acetate,and the pure 1,4-disubstituted triazole product was then obtained by elution with pure ethyl acetate.

Reference： [1]Molecules,2017,vol. 22

58
[ 4231-62-3 ]
[ 766-49-4 ]
C₂₁H₁₄FNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; tetrabutyl-ammonium chloride; benzoic acid anhydride; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; for 16h; Irradiation; regioselective reaction;

Reference： [1]Teders, Michael; Pitzer, Lena; Buss, Stefan; Glorius, Frank [ACS Catalysis, 2017, vol. 7, # 6, p. 4053 - 4056]

59
[ 766-49-4 ]
[ 171032-87-4 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1110 - 1113
[2]RSC Advances,2018,vol. 8,p. 14829 - 14832

60
[ 766-49-4 ]
[ 83012-13-9 ]
C₁₉H₈F₇N [ No CAS ]

Reference： [1]CrystEngComm,2018,vol. 20,p. 2316 - 2323

61
[ 110-89-4 ]
[ 766-49-4 ]
[ 100-52-7 ]
C₂₀H₂₀FN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With silver carbonate; In neat (no solvent); at 110℃; for 1.5h;	3.0 mol% of Ag2CO3 catalyst, 1.0 mol of benzaldehyde, 1.1 mol of piperidine, and 1.2 mol of o-fluorophenylacetylene were placed in a 10 ml reaction tube, and the reaction was stirred at 110 C for 90 minutes in a yield of 93%.

Reference： [1]Patent: CN107935801,2018,A .Location in patent: Paragraph 0055-0056
[2]Applied Organometallic Chemistry,2019,vol. 33

62
[ 75-22-9 ]
[ 1246242-17-0 ]
[ 766-49-4 ]
C₁₁H₁₇BFNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With (2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl)AuNTf<SUB>2</SUB> In dichloromethane at 20℃; for 3h; regiospecific reaction;

Reference： [1]Yang, Ji-Min; Zhao, Yu-Tao; Li, Zi-Qi; Gu, Xue-Song; Zhu, Shou-Fei; Zhou, Qi-Lin [ACS Catalysis, 2018, vol. 8, # 8, p. 7351 - 7355]

63
[ 766-49-4 ]
[ 1224739-02-9 ]

Yield	Reaction Conditions	Operation in experiment
42%	With N-Bromosuccinimide; In water; acetone; at 20℃; for 0.666667h;Green chemistry;	General procedure: To a solution of alkyne (0.5 mmol), NXS (2.00 mmol), acetone (3 mL), H2O (2.5 mmol)and Sol Gel polymer (15% wt.). The reaction solution was stirring 40 min at room temperature.When TLC showed full consumption of starting material, reaction was placed in a centrifugedtube. Supernatant was separated from the Sol Gel polymer and filtered. Filtrate was collected andsolvent was removed using the rotary evaporator. The mixture was purified by flashchromatography on Silica Gel 60 to give pure product
89 mg	With sulfuric acid; lithium perchlorate; potassium bromide; at 10 - 20℃; for 4.25h;Electrochemical reaction; Electrolysis; Green chemistry;	General procedure: Under air condition, 0.5 mmol substrate (alkyne derivatives), 1.5 mmol KBr and 0.5 mmol LiClO4 were dissolved in 10 mL H2SO4 (0.6 M) in the anodiccompartment, while 0.5 mmol LiClO4 was dissolved in 10 mL H2SO4 (0.6 M) in the cathodiccompartment. Both electrolysis compartments were equipped with Pt electrode (1.5x1.5 cm2 ) and seperated by a cation selective permeable membrane (TRJCM Type, 1.5x1.5 cm2). The reaction was conducted in 15 mA constant electric current at room temperature (10-20 C). After that, the product in the anodiccompartment was extracted by ethyl acetate. The organic phase was dried by anhydrous sodium sulfate followed by evaporation, the residue was purified by column chromatography (petroleum ether/ethyl acetate) to give the corresponding product.

Reference： [1]Molecules,2018,vol. 23
[2]Chinese Chemical Letters,2020,vol. 31,p. 1855 - 1858

64
[ 31253-08-4 ]
[ 766-49-4 ]
ethyl (E)-4-(2-fluorophenyl)-4-iodo-2-methylbut-3-enoate [ No CAS ]
ethyl (Z)-4-(2-fluorophenyl)-4-iodo-2-methylbut-3-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44.444 % de	With iron(III) trifluoromethanesulfonate; tert-butyl peroxyacetate In tert-butyl methyl ether at 20℃; for 12h; Schlenk technique; Inert atmosphere; Overall yield = 97 %; Overall yield = 168.8 mg;	Iron-Catalyzed Carboiodination of But-3-yn-2-one (1a); (Z)-3-Iodo-5-methylhept-3-en-2-one (3, E/Z = 1:12); Typical Procedure General procedure: To a flame-dried Schlenk tube was added Fe(OTf) 3 (25 mg, 0.05 mmol,10 mol%), followed by the addition of MTBE (2 mL) under N 2 atmo-sphere. Then but-3-yn-2-one (1a; 34 mg, 0.5 mmol, 1 equiv), 2-io-dobutane (2a; 276 mg, 1.5 mmol, 3 equiv), and tert-butyl peroxyace-tate (66 mg, 0.5 mmol, 1 equiv) were added sequentially. The mixturewas stirred at r.t. for 12 h. Afterwards, the reaction solution was dilut-ed with EtOAc and filtered through a plug of diatomite. The filtratewas concentrated by rotary evaporation under reduced pressure andthe residue was purified by column chromatography on silica gel(EtOAc/PE 100:1) to afford product 3 as a pale yellow liquid; yield:90.7 mg (0.36 mmol, 72%).

Reference： [1]Deng, Weili; Li, Yajun; Li, You-Gui; Bao, Hongli [Synthesis, 2018, vol. 50, # 15, p. 2974 - 2980]

65
[ 14804-38-7 ]
[ 766-49-4 ]
4‐fluoro‐2‐(2‐fluorophenyl)‐1,3‐bis(4‐methoxy‐3,5‐dimethylphenyl)azulene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 12966 - 12970
Angew. Chem.,2018,vol. 130,p. 13148 - 13152,5

66
[ 14804-38-7 ]
[ 766-49-4 ]
5‐((2‐fluorophenyl)ethynyl)‐2‐methoxy‐1,3‐dimethylbenzene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 12966 - 12970
Angew. Chem.,2018,vol. 130,p. 13148 - 13152,5

67
[ 1612-65-3 ]
[ 766-49-4 ]
C₁₈H₁₆FN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With gold(III) chloride hydrate; monoamine oxidase type N D₅ In aq. phosphate buffer at 37℃; for 16h; Enzymatic reaction;

Reference： [1]Odachowski, Marcin; Greaney, Michael F.; Turner, Nicholas J. [ACS Catalysis, 2018, vol. 8, # 11, p. 10032 - 10035]

68
[ 766-49-4 ]
[ 13440-07-8 ]
1-(naphthalen-1-yl)-3-(2-fluorophenyl)benzo[de]phosphanaphthalene-1-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With phenyl isopropyl hydroperoxide; copper(I) bromide; In ethanol; at 70℃;	2-fluorophenylacetylene (0.060 g, 0.5 mmol) was added to the reaction flask.Dinaphthylphosphorus (0.30 g, 1 mmol),CuBr (0.014 g, 0.1 mmol), phenyl isopropyl hydroperoxide(0.46 g, 3 mmol), and ethanol (2 mL),70oC reaction;TLC tracks the reaction until it is completely over;The crude product obtained after the completion of the reaction was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to give the desired product.(Yield 78%).

Reference： [1]Patent: CN109096336,2018,A .Location in patent: Paragraph 0032

69
[ 766-49-4 ]
[ 336-59-4 ]
[ 149551-70-2 ]
6-(2-fluorophenyl)-3-(perfluoropropyl)-4-(2-(thiophen-2-yl)ethyl)-1,2,4-triazin-5(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With copper(l) iodide; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran; hexane at 50℃; for 15h; Sealed tube; Glovebox; Inert atmosphere;	General procedure of the synthesis of 4 General procedure: In a glove box filled with nitrogen, to an oven-dried 5 mL pressure tube equipped with a stir bar were added CuI (0.015 mmol, 2.9 mg, 0.050 equiv), 4,4'-di-tert-butyl-2,2'-dipyridine (2.0 mg, 0.0075 mmol, 0.025 equiv), azide compounds (0.36 mmol, 1.2 equiv), terminal alkynes (0.30 mmol, 1.0 equiv), (CF3CF2CF2CO)2O (0.39 mmol, 159.9 mg, 1.3 equiv), Et3N (0.45 mmol, 45.5 mg, 1.5 equiv) and THF/n-C6H14 (1:2, 1.0 mL). The tube was sealed with Teflon screw cap and the solution was stirred at 50 °C for 15 h. The reaction mixture was cooled to room temperature and was filtered through a layer of Celite, eluted with dichloromethane. The solvent was removed by rotary evaporation and the resulting product was purified by column chromatography on silica gel with n-pentane/ dichloromethane.

Reference： [1]Lin, Bo; Wu, Wei; Weng, Zhiqiang [Tetrahedron, 2019, vol. 75, # 19, p. 2843 - 2847]

70
[ 766-49-4 ]
[ 77-75-8 ]
C₁₄H₁₃FO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine; copper(l) chloride; In N,N-dimethyl acetamide; at 80℃; for 4.0h;	General procedure: The measurement of catalytic activity and selectivity was the following procedure. Pd(II)-AOFs (0.01mmol) and CuCl (0.5mmol) were added to a solution of phenylacetylene (0.5mmol), 3-methyl-1-pentyn-3-ol (0.5mmol) and Et3N (1mmol) in DMAc (15mL). After the mixture was stirred and refluxed for 4h in 80 C oil bath. The crude products were washed by distilled water, and separation by column chromatography. The used catalyst was separated by fltration, washed with ethyl acetate and distilled water, dried at room temperature, and then can be re-used for catalytic performance experiment

Reference： [1]Catalysis Letters,2019,vol. 149,p. 2390 - 2396

71
[ 766-49-4 ]
[ 2114-36-5 ]
C₁₇H₁₅F [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With copper(I) thiophene-2-carboxylate; C55H70N3O2P; caesium carbonate; In diethyl ether; at 20℃; for 18.0h;Inert atmosphere; Schlenk technique;	General procedure: General Method A: Under the protection of argon gas, an oven-dried Schlenk tube equipped with a magnetic stir bar was added with CuTc (1.9 mg, 0.010 mmol, 5.0 mol% equivalent) and the ligand L13 (12.5 mg, 0.015 mmol, 7.5 mol% equivalent). , Cs2CO3 (130.4 mg, 0.40 mmol, 2.0 equivalents) and anhydrous Et2O (4.0 mL). Then, an alkyl halide (0.30 mmol, 1.5 equivalent) and an alkyne (0.20 mmol, 1.0 equivalent) were sequentially added to the mixture, and the mixture was stirred at room temperature for 24 to 72 hours. After the reaction is complete (monitored by TLC), the precipitate is filtered off and washed with Et2O or petroleum ether, then the solution is evaporated and purified by silica gel column chromatography to obtain the desired product

Reference： [1]Nature Chemistry,2019,vol. 11,p. 1158 - 1166
[2]Patent: CN110627610,2019,A .Location in patent: Paragraph 0445-0446; 0489-0492

72
[ 766-49-4 ]
2,2-dichloro-1-(2-fluorophenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydrogenchloride; sulfuric acid; lithium perchlorate; In water; acetonitrile; at 10 - 20℃; for 4.25h;Electrochemical reaction; Electrolysis; Green chemistry;	General procedure: Under air condition, 0.5 mmol substrate (alkyne derivatives) and 0.5 mmol LiClO4 were dissolved in 8 mL MeCN and 2 mL HCl (1.2 M, aq.) in the anodiccompartment, while 0.5 mmol LiClO4 was dissolved in 10 mL H2SO4 (0.6 M) in the cathodiccompartment. Both electrolysis compartments were equipped with Pt electrode (1.5x1.5 cm2 ) and seperated by a cation selective permeable membrane (TRJCM Type, 1.5x1.5 cm2). The reaction was conducted in 15 mA constant electric current at room temperature (10-20 C). After that, the product in the anodiccompartment was extracted by ethyl acetate. The organic phase was dried by anhydrous sodium sulfate followed by evaporation, the residue was purified by column chromatography (petroleum ether/ethyl acetate) to give the corresponding product.

Reference： [1]Chinese Chemical Letters,2020,vol. 31,p. 1855 - 1858
[2]Chemical Communications,2019,vol. 55,p. 14299 - 14302

73
[ 14062-05-6 ]
[ 766-49-4 ]
(E)-1-fluoro-2-(1-iodo-2-tosylvinyl)benzene [ No CAS ]

Reference： [1]Chinese Chemical Letters,2020

74
[ 2436-85-3 ]
[ 766-49-4 ]
[ 1007120-40-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tris-(dibenzylideneacetone)dipalladium(0); cyclohexyldiphenylphosphine; methyl trifluoromethanesulfonate; sodium t-butanolate; In tetrahydrofuran; 1,4-dioxane; at 120℃; for 2.0h;Schlenk technique; Inert atmosphere;	General procedure: In an oven dried 25 mL Schlenk tube was charged with 1 (0.2 mmol), Pd2(dba)3 (0.001 mmol, 0.5 mol %), PPh2Cy (0.004 mmol, 2 mol %) and NaOtBu (0.4 mmol, 2.0 equiv), after charging N2 for three times, the terminal alkynes 2 (0.24 mmol, 1.2 equiv), MeOTf (0.5mmol, 2.5 equiv.), THF (2 mL) and dioxane (1 mL) were added. The reaction mixture was reacted at 120 C for 2 h. After completion of the reaction, the reaction mixture was concentrated under vacuum. The desired product was isolated by column chromatography over silica gel (300-400 mesh) using petroleum ether-ethyl acetate as eluent.

Reference： [1]Tetrahedron Letters,2020

75
[ 766-49-4 ]
bis(o-fluorophenylethynyl)selenide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With selenium; silver fluoride; In dimethyl sulfoxide; at 50℃; for 10.0h;	General procedure: An oven-dried screw-capped 8-mL vial equipped with a magnetic stir bar was charged with 1a (0.6 mmol, 61.2 mg, 66 muL), 2 (0.6 mmol, 47.3 mg), AgF (2 equiv, 76.1 mg). DMSO (3 mL) was added via syringe and the mixture was stirred at 50 C for 10 h. The filtrate was diluted with ethyl acetate (50 mL) and washed with water (20 mL × 3). The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography with EtOAc and PE.

Reference： [1]Tetrahedron,2020

76
[ 766-49-4 ]
1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-5-iodouracil [ No CAS ]
1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-5-[(2-fluorophenyl)ethynyl]uracil [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 50℃; for 0.08333330000000001h;Microwave irradiation;	General procedure: The appropriate alkynes (0.60 mmol), Pd(PPh3)4 (69 mg,0.06 mmol), CuI (11 mg, 0.06 mmol), triethylamine (47 mul,0.60 mmol) and 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-beta-Dribofuranosyl)-5-iodouracil (11) (100 mg, 0.20 mmol), in 1.0mL of anhydrous DMF, were irradiated in a microwave apparatus(200 Watt maximum power) at 50 for 5 minutes.The reaction mixture was concentrated under reduced pressureand the crude residue was purified by flash chromatographyon silica gel. The purified material was dried in vacuoto afford the corresponding derivatives 12a-d, 14 in 72-84%yields, as colorless foams.2.10.1. 1-(2-O-Acetyl-5-O-benzoyl-3-deoxy-beta-D-ribofuranosyl)-5-[(2-fluorophenyl)ethynyl]uracil (12a)80 mg, 81%; [alpha]D22 = = -4 (c 0.22, CHCl3); Rf = 0.19 (EtOAc/Hexane 5:5); lambdamax 336 nm (epsilon9320); 1HNMR (300MHz,CDCl3): delta 8.66 (brs, 1H, NH), 8.04 (d, 2H, J = 7.6 Hz,Bz), 7.79 (s, 1H, H-6), 7.42-7.35 (m, 5H, Bz, 4 ArH), 7.08 (t,2H, Bz), 5.81 (d, 1H, J1-2 = 2.5 Hz, H-1), 5.43 (s, 1H, H-2), 4.70-4.65 (m, 2H, H-4 ,H-5b), 4.34 (dd, 1H, J4-5a =6.2 Hz, J5a-5b = 11.6 Hz, H-5a), 2.44-2.34 (m, 1H, H-3),2.23-2.16 (m, 1H, H-3), 2.13 (s, 3H, OAc); 13C NMR (75.5MHz, CDCl3): delta 170, 32, 165.89, 161.65, 160.78, 150.83,142.19, 133.98, 133.15, 129.99, 128.13, 126.81, 123.53,115.21, 109.42, 101.94, 100.82, 93.15, 86.23, 74.01, 73.32,66.12, 32.23, 21.18; Mass (M+H)+: 493.13; Anal. Calcd. forC26H21FN2O7: C, 63.41; H, 4.30; F, 3.86; N, 5.69% Found:C, 63.61; H, 4.50; F, 4.16; N, 5.49%

Reference： [1]Medicinal Chemistry,2020,vol. 16,p. 368 - 384

77
[ 766-49-4 ]
[ 84500-33-4 ]
1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-[(2-fluorophenyl)ethynyl]uracil [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 50℃; for 0.08333330000000001h;Microwave irradiation;	General procedure: Mixtures of the appropriate alkynes (0.60 mmol),Pd(PPh3)4 (23 mg, 0.02 mmol), CuI (3.8 mg, 0.02 mmol),triethylamine (83 mul, 0.34 mmol) and 1-(2,3,5-tri-Oacetyl-beta-D-ribofuranosyl)-5-iodouracil (2) (100 mg, 0.20mmol) in 1.0 mL of anhydrous DMF, were irradiated in amicrowave apparatus (200 Watt maximum power) for 5minutes at 50 . The reaction mixture was concentrated under reduced pressure and the crude residue was purified byflash chromatography on silica gel. The purified materialwas dried in vacuo to afford the corresponding derivatives3a-d, 5 in 65-83% yields, as colorless foams.2.5.1. 1-(2,3,5-Tri-O-acetyl-beta-D-ribofuranosyl)-5-[(2-fluorophenyl)ethynyl]uracil (3a)80 mg, 82%; [alpha]D22 = - 4 (c 0.22, CHCl3); Rf = 0.19 (EtOAc/Hexane 5:5); lambdamax 340 nm (epsilon 8250);1HNMR (300MHz,CDCl3): delta 8.65 (brs, 1H, NH), 7.89 (s, 1H, H-6), 7.53-7.50 (m, 1H, ArH), 7.35-7.30 (m, 1H, ArH), 7.13-7.06 (m,2H, ArH), 6.14 (d, 1H, J1-2 = 4.6Hz, H-1), 5.38-5.35 (m,2H, H-2, H-4), 4.41-4.38 (m, 3H, H-3, H-5a, H-5b),2.21, 2.13, 2.12 (3s, 9H, 3OAc); 13C NMR (75.5 MHz, CDCl3):delta 169.00, 168.62, 168.34, 159.23, 148.00, 140.17,132.53, 128.84, 128.32, 125.54, 121.63, 100.23, 89.92,86.45, 83.03, 79.80, 72.24, 69.55, 61.53, 19.84, 19.50, 19.31;Mass (M+H)+: 489.12; Anal. Calcd. for C23H21FN2O9: C,56.56; H, 4.33; N, 5.74; F, 3.89% Found: C, 56.86; H, 4.08;N, 5.94; F, 3.79%.

Reference： [1]Medicinal Chemistry,2020,vol. 16,p. 368 - 384

78
[ 766-49-4 ]
1-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-C-methyl-β-D-ribofuranosyl)-5-iodouracil [ No CAS ]
1-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-C-methyl-β-D-ribofuranosyl)-5-[(2-fluorophenyl)ethynyl]uracil [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 50℃; for 0.08333330000000001h;Microwave irradiation;	General procedure: A mixture of the appropriate alkyne (0.54 mmol),Pd(PPh3)4 (20 mg, 0.017 mmol), CuI (3.2 mg, 0.017 mmol),triethylamine (47 mul, 0.34 mmol) and 1-(2-O-acetyl-5-Obenzoyl-3-deoxy-beta-D-ribofuranosyl)-5-iodouracil (17) (100mg, 0.17 mmol), in 1.0 mL of anhydrous DMF, was irradiatedin a microwave apparatus (200 Watt maximum power)at50 for 5 minutes. The reaction mixture was concentratedunder reduced pressure and the crude residue was purified byflash chromatography on silica gel. The purified materialwas dried in vacuo to afford the corresponding derivatives18a-d, 20 in 76-92% yields, as colorless foams.2.13.1. 1-(2-O-Acetyl-5-O-benzoyl-3-deoxy-3-C-methyl-beta-D-ribofuranosyl)-5-[(2-fluorophenyl)ethynyl]uracil (18a)74 mg, 86%; [alpha]D22 = -3 (c 0.31, CHCl3); Rf = 0.19 (EtOAc/Hexane 5:5); lambdamax 342 nm (epsilon 8970); 1HNMR (300MHz,CDCl3): delta 8.29 (brs, 1H, NH), 8.04 (d, 2H, J = 8.0 Hz,Bz), 7.86 (s, 1H, H-6), 7.36-7.29 (m, 5H, Bz, 4 ArH), 7.07(dd, 2H, J = 8.0 Hz, J = 15.6, Bz), 5.78 (brs, 1H, H-1), 5.51(d, 1H, J2-3 = 6.2 Hz, H-2), 4.71-4.57 (m, 2H, H-4,H-5a),4.34 (dd, 1H, J4-5b = 3.8 Hz, J5a-5b = 11.6 Hz, H-5b), 2.55-2.45 (m, 1H, H-3), 2.17 (s, 3H, OAc), 1.09 (d, 3H, JCH3-3=6.8 Hz, CH3); 13C NMR (75.5 MHz, CDCl3): delta 170, 32,165.89, 161.62, 160.75, 150.83, 142.19, 133.98, 133.15,129.99, 128.13, 126.81, 123.53, 115.21, 109.42, 100.82,96.15, 93.15, 86.23, 81.23, 63.32, 35.23, 21.18, 10.02; Mass(M+H)+: 507.15; Anal. Calcd. for C27H23FN2O7: C, 64.03; H,4.58; F, 3.75; N, 5.53% Found: C, 64.23; H, 4.38; F, 3.55; N,5.33%.

Reference： [1]Medicinal Chemistry,2020,vol. 16,p. 368 - 384

79
[ 766-49-4 ]
[ 133745-75-2 ]
[ 342-24-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	With tert.-butylhydroperoxide; water; copper(II) sulfate In acetonitrile at 80℃; for 4h; Schlenk technique; Inert atmosphere;

Reference： [1]Chen, Hanfei; Cheng, Hao; Huang, Yifan; Jin, Chaochao; Song, Weihan; Tan, Chen; Tan, Jiajing; Tang, Lin; Yang, Fang; Zhang, Shuaifei [Organic Letters, 2020]

80
[ 766-49-4 ]
N,N,N-trimethylbenzeneaminium trifluoromethanesulfonate [ No CAS ]
[ 208183-93-1 ]

Yield	Reaction Conditions	Operation in experiment
94.9%	With sodium carbonate In N,N-dimethyl acetamide; water for 2h; Electrolysis;	3.1-3.3 The preparation method of a 3-aryl-2-propyn-1-ol derivative is completed according to the following steps: 1. Add 0.2mmol 1-ethynyl-2-fluorobenzene,0.36mmol N,N,N-trimethylanilinium trifluoromethanesulfonate,0.4mmol sodium carbonate,1.4mmol water,4mL N,N-dimethylacetamide was added to a 25mL three-necked flask in turn,Install two platinum plate electrodes in the three-necked flask,Connect the two platinum plate electrodes to the power source,At room temperature,Electrolysis for 2h under air atmosphere and stirring conditions,To obtain a reaction mixture;The electrolysis current described in step one is 15mA constant current;The dimensions of the two platinum plate electrodes mentioned in step one are both 10×10×0.1mm,The distance between the two platinum plate electrodes is 2cm;2. Pour the reaction mixture into 15mL brine,Use ethyl acetate to extract 3 times,Combine the organic layers;Then use anhydrous Na2SO4 to dry the combined organic layer,Finally, the solvent is removed by vacuum distillation,Get a crude product;The brine described in step two is saturated brine;The power supply described in step two is a potentiostat;The temperature of the vacuum distillation described in step two is 35°C,The pressure is 0.1MPa;3. Purify the crude product by silica gel column chromatography,among them,The eluent is a mixture of ethyl acetate/petroleum ether,The 3-aryl-2-propyn-1-ol derivatives are obtained.The volume ratio of ethyl acetate to petroleum ether in the mixture of ethyl acetate/petroleum ether described in step 3 is 1:5.The reaction equation of Example 3 is: The purity of the 3-aryl-2-propyn-1-ol derivatives prepared in Example 3 was 99%,The yield was 94.9%,

Reference： [1]Current Patent Assignee: HARBIN INSTITUTE OF TECHNOLOGY - CN112110800, 2020, A Location in patent: Paragraph 0068-0081

81
[ 766-49-4 ]
[ 111409-79-1 ]
[ 84379-72-6 ]
(E)-(3-(2-fluorophenyl)-5,5-dimethylhex-3-en-1-yn-1-yl)triisopropylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With manganese; nickel(II) bromide diethylene glycol dimethyl ether; 4,4'-Dimethoxy-2,2'-bipyridin; lithium bromide; In N,N-dimethyl acetamide; at 20℃; for 24h;Inert atmosphere; Sealed tube;	General procedure: In a N2-filledglovebox, to an oven-dried 5 mL vial equipped with a magnetic stir bar was addedalkyne substrate (1.0 equiv., 0.1 mmol), alkynyl bromide (1.2 equiv., 0.12 mmol), NHPI ester (2.5 equiv., 0.25 mmol), NiBr2•diglyme (10 mmol%), Ligand 1 (12 mol%),Mn powder (2.5 equiv., 0.25 mmol) and LiBr (0.5 equiv., 0.05 mmol) (unlessotherwise noted). The mixture was then dissolved in 0.3 mL dry DMA (unlessotherwise noted). The vial was tightly capped and removed from the glovebox. Themixture was allowed to vigorously stir at room temperature for 24 h. After thereaction was complete, the mixture was directly subjected to flash silica gel columnchromatography to afford the pure product. (*Note: for alkynyl bromide scope, 1.0equiv. of LiBr and DMSO were used instead for the preparation of 4y, 4z, 4aa; forpreparation of 4ab, 4ag, 4ap, 4aq, 4as, 3.0 equiv. of alkyne and 1.0 equiv. of alkynylbromide were used; for preparation of 4at, 1.5 equiv. of alkynyl bromide and 1.7 equiv.of C4F9I were used; for preparation of 4au, 1.5 equiv. of alkynyl bromide and 2.0equiv. of C4F9I were used; for preparation of 4av, 3 equiv. of alkyne and 1.0 equiv. ofalkyne bromide and 2.0 equiv. of C4F9I were used with Ligand 7)

Reference： [1]Chem,2021,vol. 7,p. 993 - 1005

82
[ 2564-83-2 ]
[ 766-49-4 ]
1-(2-fluorophenyl)-2-(2,2,6,6-tetramethylpiperidin-1-yl)-2-selenoxoethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With selenium; silver fluoride In N,N-dimethyl acetamide at 50℃; for 10h;	5 Example 5 Synthesis of 1-(2-fluorophenyl)-2-(2,2,6,6-tetramethylpiperidinyl)-2-selenoacetamide (33) Weigh 0.9mmol 3-fluorophenylacetylene (the compound corresponding to number (14), 0.1081g), 0.9mmol selenium powder (0.0710g), 0.3mmol 2,2,6,6-tetramethylpiperidine oxide (0.0468g), 0.9mmol of silver fluoride (0.1141g) in an 8mL reaction flask, add 3mL of N,N-dimethylacetamide as a solvent, stir and react at 50 for 10 hours; the reaction is over, the reaction solution After vacuum concentration and column chromatography separation (column chromatography separation conditions: the stationary phase is 200-300 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), the mobile phase change program (A:B) 1:20) to obtain 0.0607 g of reaction product.

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN112851566, 2021, A Location in patent: Paragraph 0054-0057

83
[ 758-21-4 ]
[ 766-49-4 ]
[ 694-53-1 ]
C₁₈H₂₅FSi₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With tris(pentafluorophenyl)borate In dichloromethane at -20℃;

Reference： [1]Gao, Liuzhou; Li, Guoao; Li, Shuhua; Liu, Xueting; Su, Xiaoshi; Wang, Guoqiang [Chemical Science, 2021, vol. 12, # 32, p. 10883 - 10892]

84
[ 766-49-4 ]
[ 607-81-8 ]
diethyl 4-(2-fluorophenyl)spiro[4.5]deca-3,6,9-triene-2,2-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With tripotassium phosphate tribasic In acetonitrile at 20℃; for 24h; Irradiation; Inert atmosphere; Schlenk technique;

Reference： [1]Rehbein, Julia; Reiser, Oliver; Zhao, Quan-Qing [Green Chemistry, 2022, vol. 24, # 7, p. 2772 - 2776]

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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 766-49-4 ] {[proInfo.proName]}

Quality Control of [ 766-49-4 ]

Related Doc. of [ 766-49-4 ]

Product Details of [ 766-49-4 ]

Calculated chemistry of [ 766-49-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 766-49-4 ]

Application In Synthesis of [ 766-49-4 ]

[ 766-49-4 ] Synthesis Path-Upstream 1~14

[ 766-49-4 ] Synthesis Path-Downstream 1~84

Related Functional Groups of [ 766-49-4 ]

Fluorinated Building Blocks

Aryls

Alkynes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

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[ 766-49-4 ]