[ CAS No. 886-66-8 ] {[proInfo.proName]}

Name: 886-66-8|1,4-Diphenylbutadiyne|98%
Brand: Ambeed
SKU: A513377
Price: 7.0 USD
Availability: InStock
Rating: 96 (29 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 886-66-8 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 886-66-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 886-66-8 ]

SDS Specification

Alternatived Products of [ 886-66-8 ]

Product Details of [ 886-66-8 ]

CAS No. :	886-66-8	MDL No. :	MFCD00004787
Formula :	C₁₆H₁₀	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HMQFJYLWNWIYKQ-UHFFFAOYSA-N
M.W :	202.25	Pubchem ID :	70174
Synonyms :

Calculated chemistry of [ 886-66-8 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	66.64
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.25
Log Po/w (XLOGP3) :	5.17
Log Po/w (WLOGP) :	3.25
Log Po/w (MLOGP) :	5.67
Log Po/w (SILICOS-IT) :	4.33
Consensus Log Po/w :	4.33

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.91
Solubility :	0.00251 mg/ml ; 0.0000124 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.92
Solubility :	0.00245 mg/ml ; 0.0000121 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.08
Solubility :	0.00166 mg/ml ; 0.00000822 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.57

Safety of [ 886-66-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 886-66-8 ]

* 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 [ 886-66-8 ]
Downstream synthetic route of [ 886-66-8 ]

[ 886-66-8 ] Synthesis Path-Upstream 1~3

1
[ 1262020-28-9 ]
[ 90-59-5 ]
[ 886-66-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(II) acetate monohydrate In N,N-dimethyl-formamide at 110℃; for 5 h;	General procedure: Propargylic alcohol (0.2 mmol) in acetonitrile (2.0 mL) was added Cu(OAc)2·H2O (0.1 mmol) at room temperature. The reaction mixture was heated at reflux, in air. After completion of the reaction as indicated by TLC, the solvent was removed under reduced pressure,and the residue was purified by chromatography on silica gel (100−200 mesh) using petroleum ether/EtOAc (9/1, v/v) as the eluent to give 1,3-butadiynes.

Reference： [1] Journal of Chemical Research, 2013, vol. 37, # 9, p. 546 - 549

2
[ 1122-91-4 ]
[ 536-74-3 ]
[ 886-66-8 ]
[ 57341-98-7 ]

Reference： [1] Chemical Communications, 1997, # 14, p. 1275 - 1276

3
[ 288-47-1 ]
[ 536-74-3 ]
[ 35070-01-0 ]
[ 886-66-8 ]
[ 1263057-86-8 ]

Reference： [1] Journal of Organic Chemistry, 2012, vol. 77, # 12, p. 5381 - 5388

[ 886-66-8 ] Synthesis Path-Downstream 1~87

1
[ 886-66-8 ]
[ 1445-78-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodiumsulfide nonahydrate; dimethyl sulfoxide; potassium hydroxide; at 80℃; for 4h;	General procedure: A solution of 1,4-diaryl-1,3-butadiynes (1) (1.0 mmol), KOH (0.3 mmol), and H2O (2.0 mmol), or RNH2 (1.5 mmol), or Na2S*9H2O (2.0 mmol) in DMSO (2.0 mL) was heated at 80 C with stirring for 4 h. The reaction mixture was then cooled to room temperature, and the volatiles were removed under reduced pressure. The obtained residue was subjected to silica gel column chromatography (eluting with CH2Cl2/petroleum ether: 0:1 to 1:10) to give 2,5-diaryl-substituted five-membered heterocycles.

Reference： [1]Tetrahedron,2014,vol. 70,p. 8252 - 8256
[2]European Journal of Organic Chemistry,2019,vol. 2019,p. 6690 - 6696
[3]Organic Letters,2014,vol. 16,p. 6156 - 6159
[4]Journal of Organic Chemistry,2020,vol. 85,p. 12922 - 12934
[5]Journal of Organic Chemistry,1992,vol. 57,p. 3895 - 3901
[6]Tetrahedron,1996,vol. 52,p. 12677 - 12698
[7]Tetrahedron,1996,vol. 52,p. 12677 - 12698
[8]Tetrahedron,1996,vol. 52,p. 12677 - 12698
[9]Tetrahedron,1996,vol. 52,p. 12677 - 12698
[10]Tetrahedron,1996,vol. 52,p. 12677 - 12698
[11]Tetrahedron,1996,vol. 52,p. 12677 - 12698
[12]Tetrahedron,1996,vol. 52,p. 12677 - 12698
[13]Beilstein Journal of Organic Chemistry,2011,vol. 7,p. 1499 - 1503
[14]Tetrahedron Letters,2014,vol. 55,p. 52 - 55
[15]Journal of the American Chemical Society,2020,vol. 142,p. 8130 - 8135
[16]Organic Letters,2021,vol. 23,p. 7650 - 7655

2
[ 7436-90-0 ]
[ 886-66-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In acetonitrile at 110℃; Schlenk technique; Inert atmosphere;	General procedure for 1,3-dialkynes synthesis General procedure: In an oven-dried Schlenk tube under nitrogen atmosphere were added dibromoalkene 1 (0.50 mmol), CuI (10 mol%), 1,10-phenthroline (20 mol%), and Cs2CO3 (1.0 mmol) followed by the addition of CH3CN (0.5 mL). The resulting reaction mixture was stirred at 110 °C for 20-24 h. Progress of the reaction was monitored by TLC until the reaction is completed. The reaction mixture was quenched by the addition of aq. NH4Cl solution and extracted with CH2Cl2 (3 10 mL). The organic layers were dried (Na2SO4) and concentrated in vacuo. Purification of the residue on a silica gel column chromatography using petroleum ether/ethyl acetate as eluent furnished the 1,3-dialkynes 2.
89%	With pyridine; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1-methyl-pyrrolidin-2-one at 90℃; for 2h; Schlenk technique; Inert atmosphere;	Representative coupling procedure General procedure: A mixture of 1-(2,2-dibromovinyl)-4-methylbenzene (0.207 g, 0.75 mmol, 1 equiv), K3PO4 (0.48 g, 2.25 mmol,3 equiv), pyridine (0.03 g, 0.375 mmol, 0.5 equiv), Pd(PPh3)4 (0.017 g,0.015 mmol, 0.02 equiv), and NMP (5 mL) was heated at 90 C for 2 h in anoven-dried 50 mL Schlenk tube under nitrogen atmosphere. The contents werecooled to room temperature, quenched with water, and extracted with ethylacetate. The combined extract was treated with brine followed by anhydrousMgSO4 and concentrated. The crude was purified by column chromatographyusing silica gel and petroleum ether as eluent
87%	With copper(l) iodide; potassium iodide In N,N,N,N,N,N-hexamethylphosphoric triamide at 120℃; for 12h;

86%	With 3-nitropyridine; caesium carbonate In dimethyl sulfoxide at 120℃; for 12h; regioselective reaction;	. General experimental procedure for the synthesis of 1,3 diynes 2a-c, e-g, i-k, o using (2,2-dibromovinyl)arenes 4a-j. General procedure: A 10 mL reaction vial was charged with a (2,2-dibromovinyl)arenes 4a-j (1.0 mmol), cesium carbonate (1.0 mmol), DMSO (1 mL) and 10 mol% 3-nitopyridine. The reaction vial was then heated at 120 °C for 12 h. After completion of the reaction (progress was monitored by TLC; SiO2, Hexane/EtOAc = 9.5:0.5), the mixture was diluted with ethyl acetate (15 mL) and water (20 mL) and extracted with ethyl acetate (3 × 10 mL). The combined organic layer was washed with brine (3 × 10 mL) and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and the remaining residue was purified by column chromatography over silica gel using hexane / ethyl acetate (9.5:0.5) as an eluent to obtain the desired products 2a-c, e-g, i-k, o in high yields.
82%	With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;
80%	With t-AmONa-NiCRA-bpy In tetrahydrofuran; hexane
72%	With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 25℃;
71%	With potassium <i>tert</i>-butylate In toluene at 120℃; for 4h;
71%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; trifuran-2-yl-phosphane In N,N-dimethyl-formamide at 80℃;
67%	With (1,10-phenanthroline)(triphenylphosphine)CuBr; benzamide; caesium carbonate In dimethyl sulfoxide at 80℃; for 3h;
	With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 60℃;
	Multi-step reaction with 2 steps 1: caesium carbonate / dimethyl sulfoxide / 8 h / 120 °C 2: piperidine; iodine / water / 12 h / 100 °C
	With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 25℃; Sealed tube;	General procedure for the synthesis of symmetric 1,3-diynes 1a-i General procedure: The compounds were prepared according to a published procedure.3 Toa sealed tube were added DMSO (2.0 mL), the appropriate (2,2dibromovinyl)benzene (1.0 mmol), CuI (20 mol%, 0.038 g), DBU (2.0 mmol,0.304 g). The mixture was stirred at room temperature (25 °C) for 8-12 h. Then asaturated sodium chloride solution (10.0 mL) was added, and the product wasextracted with ethyl acetate (3x 15.0 mL). The organic layer was separated,dried with MgSO4 and concentrated under vacuum. The residue was purified by column chromatography using silica gel and eluted with hexane/ethylacetate in different proportions. Yields: 45-90%.

Reference： [1]Mahendar, Lodi; Ramulu, Bokka Venkat; Satyanarayana, Gedu [Synthetic Communications, 2017, vol. 47, # 12, p. 1151 - 1158]
[2]Rao, Maddali L.N.; Dasgupta, Priyabrata; Ramakrishna, Boddu S.; Murty, Venneti N. [Tetrahedron Letters, 2014, vol. 55, # 25, p. 3529 - 3533]
[3]Suzuki, Hitomi; Aihara, Mie; Yamamoto, Hidetoshi; Takamato, Yuuko; Ogawa, Takuji [Synthesis, 1988, # 3, p. 236 - 238]
[4]Kaldhi, Dhananjaya; Vodnala, Nagaraju; Gujjarappa, Raghuram; Kabi, Arup K.; Nayak, Subhashree; Malakar, Chandi C. [Tetrahedron Letters, 2020, vol. 61, # 16]
[5]Location in patent: experimental part Coste, Alexis; Couty, Francois; Evano, Gwilherm [Synthesis, 2010, # 9, p. 1500 - 1504]
[6]Vanderesse, Regis; Fort, Yves; Becker, Sandrine; Caubere, Paul [Tetrahedron Letters, 1986, vol. 27, # 30, p. 3517 - 3520]
[7]Location in patent: experimental part Jin, Hui; Kuang, Chunxiang [Chinese Journal of Chemistry, 2011, vol. 29, # 3, p. 592 - 594]
[8]Yan, Jincan; Wang, Lei [Synthetic Communications, 2005, vol. 35, # 17, p. 2333 - 2338]
[9]Shen, Wang; Thomas, Sheela A. [Organic Letters, 2000, vol. 2, # 18, p. 2857 - 2860]
[10]Location in patent: scheme or table Das, Biswanath; Salvanna; Reddy, Gandolla Chinna; Balasubramanyam, Penagaluri [Tetrahedron Letters, 2011, vol. 52, # 48, p. 6497 - 6500]
[11]Location in patent: scheme or table Laouiti, Anouar; Rammah, Mohamed M.; Rammah, Mohamed B.; Marrot, Jerome; Couty, Francois; Evano, Gwilherm [Organic Letters, 2012, vol. 14, # 1, p. 6 - 9]
[12]Kaldhi, Dhananjaya; Vodnala, Nagaraju; Gujjarappa, Raghuram; Kabi, Arup K.; Nayak, Subhashree; Malakar, Chandi C. [Tetrahedron Letters, 2020, vol. 61, # 16]
[13]Hellwig, Paola S.; Guedes, Jonatan S.; Barcellos, Angelita M.; Perin, Gelson; Lenardão, Eder J. [Molecules, 2021, vol. 26, # 8]

3
[ 886-66-8 ]
[ 14527-26-5 ]
[ 55373-70-1 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 12677 - 12698

4
[ 886-66-8 ]
[ 538-28-3 ]
[ 17284-05-8 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 12677 - 12698

5
[ 886-66-8 ]
[ 1071-37-0 ]
[ 23460-46-0 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 12677 - 12698

6
[ 6214-35-3 ]
[ 536-74-3 ]
[ 35304-86-0 ]
[ 886-66-8 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 8591 - 8594

7
[ 106-37-6 ]
[ 1719-19-3 ]
[ 1849-27-0 ]
[ 886-66-8 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 1910 - 1913

8
[ 106-37-6 ]
[ 536-74-3 ]
[ 1849-27-0 ]
[ 886-66-8 ]
[ 13667-12-4 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 1910 - 1913

9
[ 886-66-8 ]
[ 1075-06-5 ]
(E)-2-Hydroxy-1,3,6-triphenyl-hex-3-en-5-yn-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 4664 - 4668

10
[ 672-57-1 ]
[ 536-74-3 ]
[ 868701-47-7 ]
[ 886-66-8 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 9860 - 9868

11
[ 5398-69-6 ]
[ 536-74-3 ]
5-nitro-3-phenyl-1H-isochromen-1-one [ No CAS ]
[ 886-66-8 ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 4829 - 4837

12
[ 886-66-8 ]
[ 693-02-7 ]
[ 1817-57-8 ]
1-(5'-butyl-4'-phenylethynyl-[1,1';3',1'']terphenyl-2'-yl)-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: hex-1-yne; 4-phenyl-3-butyne-2-one With 1,4-diphenyl-1,3-butadiyne; tris(2,6-dimethoxyphenyl)phosphine In toluene at 20℃; for 0.5h; Stage #2: 1,4-diphenyl-1,3-butadiyne With methylaluminoxane In toluene at 80℃; for 4h;

Reference： [1]Rubina, Marina; Conley, Matthew; Gevorgyan, Vladimir [Journal of the American Chemical Society, 2006, vol. 128, # 17, p. 5818 - 5827]

13
[ 159087-45-3 ]
[ 886-66-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With magnesium sulfate; copper(II) sulfate; In N,N-dimethyl-formamide; at 60℃; for 24h;	A mixture of 2a (0.05 mmol), CuSO4 (0.02 mmol), MgSO4 (0.1 mmol) in DMF (1 mL) was stirred at 60C under air atmosphere for 24 h. The combined organic layer was washed with brine, extracted with ethyl acetate, dried over Na2SO4, and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography to give the corresponding products.

Reference： [1]Tetrahedron,2014,vol. 70,p. 5815 - 5819
[2]Tetrahedron Letters,2005,vol. 46,p. 8661 - 8664

14
[ 24287-95-4 ]
[ 536-74-3 ]
6-phenyl-7-phenyl-ethyl-thieno[3,2-c]pyran-4-one [ No CAS ]
[ 886-66-8 ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 9554 - 9570

15
[ 1482-82-2 ]
[ 886-66-8 ]
[ 950894-31-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium tetrahydroborate; In ethanol; at 85℃;Inert atmosphere;	General procedure: To a nitrogen flushed 50 mL round bottom flask, substituted 1,3-butadiyne (2.0 mmol), either <strong>[1482-82-2]dibenzyl diselenide</strong> (1.0 mmol) or dimethyl disulfide (1.0 mmol), and 10 mL 95% ethanol were added. Sodium borohydride (6.0 mmol) was added to the reaction vial and allowed to reflux at 85o C overnight. The reaction mixture was purified via column chromatography using varying concentrations of hexanes and ethyl acetate as an eluent.

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 1529 - 1537
[2]Journal of Organic Chemistry,2007,vol. 72,p. 6726 - 6734
[3]Tetrahedron Letters,2017,vol. 58,p. 638 - 641

16
[ 603-11-2 ]
[ 886-66-8 ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 4829 - 4837

17
[ 497-25-6 ]
[ 536-74-3 ]
[ 888329-88-2 ]
[ 1483-82-5 ]
[ 886-66-8 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 833 - 835

18
[ 497-25-6 ]
[ 536-74-3 ]
[ 888329-88-2 ]
[ 886-66-8 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 833 - 835
[2]Synlett,2012,vol. 23,p. 1549 - 1553
[3]Chemical Communications,2012,vol. 48,p. 4974 - 4976
[4]Catalysis science and technology,2015,vol. 5,p. 851 - 859
[5]Catalysis science and technology,2019,vol. 9,p. 1691 - 1698

19
[ 1295-35-8 ]
[ 886-66-8 ]
[Ni₄(1,4-diphenylbutadiyne)(1,5-cyclooctadiene)] [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1995,vol. 231,p. 213 - 216
Inorg. Chim. Acta,

20
[ 11136-36-0 ]
[ 886-66-8 ]
(η5-C5Me4-(CH2)-)Ti(-C(=CHPh)C(=CHPh)CH2-η5-C5Me4) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 8313 - 8323

21
[ 1295-35-8 ]
[ 886-66-8 ]
[ 132280-91-2 ]
[ 433218-58-7 ]

Reference： [1]Organometallics,2002,vol. 21,p. 1975 - 1981

22
[ 1295-35-8 ]
[ 886-66-8 ]
[ 172096-31-0 ]

Reference： [1]Polyhedron,1995,vol. 14,p. 2879 - 2886

23
[ 1295-35-8 ]
[ 886-66-8 ]
[ 603-35-0 ]
[Ni(Ph3P)2(η2(1:2)-PhCCCCPh)] [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1995,vol. 50,p. 377 - 384

24
(2-cyanophenyl)magnesium chloride [ No CAS ]
[ 4890-63-5 ]
[ 4341-02-0 ]
[ 886-66-8 ]
[ 32183-76-9 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 6731 - 6734

25
[ 1027513-14-9 ]
[ 536-74-3 ]
[ 886-66-8 ]
[ 405-29-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 1627 - 1632

26
[ 886-66-8 ]
[ 538-81-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With (hydroxido){N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene}copper(I); hydrogen; In tetrahydrofuran; at 40℃; under 75007.5 Torr; for 17h;Autoclave;	General procedure: The autoclave is purged with N2 (1 x 1 bar, 3 x 10 bar) before the reaction vessels are placed in the autoclave under a counterflow of N2. The autoclave is purged with N2 (3 x 10 bar) and H2(3 x 20 bar) before the appropriate H2 pressure is applied (pressure is given as initial pressurebefore heating). The heating block is pre-heated before the autoclave is placed inside. After the appropriate reaction time the autoclave is allowed to cool to rt and H2 is released. The autoclave is purged with N2 (3 x 10 bar) before the reaction vessels are taken out. The reaction mixture isfiltered through a small plug of silica (1 mL, tert-butyl methyl ether as eluent), and all volatiles are removed under reduced pressure. Reactions are subsequently analyzed either by GC orNMR. The crude mixture is then subjected to purification as indicated with the appropriate substrates.

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 10660 - 10666
[2]Tetrahedron,2017,vol. 73,p. 5023 - 5028
[3]Tetrahedron,2010,vol. 66,p. 1399 - 1403
[4]Tetrahedron,2017,vol. 73,p. 5023 - 5028

27
[ 363-72-4 ]
[ 536-74-3 ]
[ 886-66-8 ]
[ 434-90-2 ]
[ 13509-88-1 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 2522 - 2523

28
[ 497-25-6 ]
potassium (2-phenylethynyl)trifluoroborate [ No CAS ]
[ 888329-88-2 ]
[ 886-66-8 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 3272 - 3275
[2]Organic Letters,2010,vol. 12,p. 3272 - 3275

29
[ 61613-20-5 ]
[ 536-74-3 ]
[ 886-66-8 ]
[ 107734-06-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 85% 2: 10%	With palladium 10% on activated carbon; triethylamine; triphenylphosphine; zinc(II) chloride In N,N-dimethyl-formamide at 110℃; for 3h; Inert atmosphere;	General procedure for the synthesis of 2-substituted indoles General procedure: 2-Iodoanilide1 (1mmol),phenyl acetylene 2 (1.05 mmol), PPh3 (0.25 mmol), 10% Pd/C (5 mol %) and ZnCl2 (10mol %) containing 27-30 mol% of water were taken together in a two necked round bottomed flask fitted with condenser. After making the system inert under argon atmosphere, 7 equiv Et3N and DMF (6 mL) were added and the reaction mixture was stirred at 110°C. The progress of the reaction was monitored by TLC. Upon completionof the reaction, the mixture was allowed to cool to r.t, diluted with water and then extracted with EtOAc (3 x 20 mL). Then the organic layer was dried over Na2SO4 and concentrated in vacuum to get crude product which was then purified through column chromatography by using silica gel ( 60-120 mesh) and pet erther : EtOAc (5:1) aseluent.
1: 71% 2: 6%	With copper diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol for 47h; Inert atmosphere; Reflux;
1: 60% 2: 12%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; copper dichloride In ethanol for 52h; Inert atmosphere; Reflux;

Reference： [1]Ahmed, Atiur; Ghosh, Munmun; Sarkar, Pompy; Ray, Jayanta K. [Tetrahedron Letters, 2013, vol. 54, # 49, p. 6691 - 6694]
[2]Wang, Ruiping; Mo, Song; Lu, Yongzhong; Shen, Zengming [Advanced Synthesis and Catalysis, 2011, vol. 353, # 5, p. 713 - 718]
[3]Wang, Ruiping; Mo, Song; Lu, Yongzhong; Shen, Zengming [Advanced Synthesis and Catalysis, 2011, vol. 353, # 5, p. 713 - 718]

30
[ 26305-75-9 ]
[ 886-66-8 ]
sodium cyclopentadienide [ No CAS ]
[ 501-65-5 ]
(η(5)-cyclopentadienyl)(.eta(4)-tetraphenylcyclobutadiene)cobalt(I) [ No CAS ]
bis[(η5-cyclopentadienyl)(η4-triphenylcyclobutadiene)cobalt] [ No CAS ]
[(η5-cyclopentadienyl)Co(η4-triphenylcyclobutadiene)]2[(η5-cyclopentadienyl)Co(η4-diphenylcyclobutadiene)] [ No CAS ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 4882 - 4891

31
[ 26305-75-9 ]
[ 886-66-8 ]
sodium (methoxycarbonyl)cyclopentadienide [ No CAS ]
[ 501-65-5 ]
[ 182627-81-2 ]
[ 1307232-76-3 ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 4882 - 4891

32
[ 536-74-3 ]
[ 886-66-8 ]
[ 612-71-5 ]
[ 1165-53-3 ]

Yield	Reaction Conditions	Operation in experiment
40%	Stage #1: phenylacetylene With palladium dichloride zirconia vibration ball mill; neat (no solvent); Stage #2: at 20℃; for 2h; neat (no solvent);

Reference： [1]Location in patent: experimental part Schmidt, Robert; Thorwirth, Rico; Szuppa, Tony; Stolle, Achim; Ondruschka, Bernd; Hopf, Henning [Chemistry - A European Journal, 2011, vol. 17, # 29, p. 8129 - 8138]

33
[ 1295-35-8 ]
[ 886-66-8 ]
[ 2071-20-7 ]
[Ni3(μ-bis(diphenylphosphino)methane)3(μ3-η(1)-C.tplbond.C(Ph))2] [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1995,vol. 233,p. 1 - 4
Inorg. Chim. Acta,

34
[ 36947-68-9 ]
[ 886-66-8 ]
[ 1340595-16-5 ]
C₂₂H₂₀N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 16h;	General procedure: To a stirred solution of indole (1.0 mmol)/Imidazole (1.2 mmol) in DMSO was added 1,3-diyne (1.0 mmol), CuI (0.1 mmol), 1,10-phenanthroline (0.05 mmol) and cesium carbonate (1.5 mmol). The reaction mixture was heated at 100 C for 5-16 h and the completion of the reaction was monitored by TLC. After completion of the reaction, it was cooled down to room temperature and then diluted with H2O (5 mL) followed by extraction of the product with EtOAc (3 × 10 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and the solvent was removed in vacuo. The crude product was purified on a silica gel column using hexane: ethyl acetate as eluent. The Z isomer was crytalised using DCM/EtOH in indole and EtOH in case of imidazole.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5752 - 5757

35
[ 670-96-2 ]
[ 886-66-8 ]
[ 1340595-18-7 ]
C₂₅H₁₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In dimethyl sulfoxide at 100℃; for 16h; optical yield given as %de; diastereoselective reaction;	General procedure: To a stirred solution of indole (1.0 mmol)/Imidazole (1.2 mmol) in DMSO was added 1,3-diyne (1.0 mmol), CuI (0.1 mmol), 1,10-phenanthroline (0.05 mmol) and cesium carbonate (1.5 mmol). The reaction mixture was heated at 100 °C for 5-16 h and the completion of the reaction was monitored by TLC. After completion of the reaction, it was cooled down to room temperature and then diluted with H2O (5 mL) followed by extraction of the product with EtOAc (3 × 10 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and the solvent was removed in vacuo. The crude product was purified on a silica gel column using hexane: ethyl acetate as eluent. The Z isomer was crytalised using DCM/EtOH in indole and EtOH in case of imidazole.

Reference： [1]Gupta, Sahaj; Agarwal, Piyush K.; Saifuddin, Mohammad; Kundu, Bijoy [Tetrahedron Letters, 2011, vol. 52, # 44, p. 5752 - 5757]

36
[ 1215-59-4 ]
[ 886-66-8 ]
[ 1340595-10-9 ]
C₃₁H₂₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In dimethyl sulfoxide at 100℃; for 10h; optical yield given as %de; diastereoselective reaction;	General procedure: To a stirred solution of indole (1.0 mmol)/Imidazole (1.2 mmol) in DMSO was added 1,3-diyne (1.0 mmol), CuI (0.1 mmol), 1,10-phenanthroline (0.05 mmol) and cesium carbonate (1.5 mmol). The reaction mixture was heated at 100 °C for 5-16 h and the completion of the reaction was monitored by TLC. After completion of the reaction, it was cooled down to room temperature and then diluted with H2O (5 mL) followed by extraction of the product with EtOAc (3 × 10 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and the solvent was removed in vacuo. The crude product was purified on a silica gel column using hexane: ethyl acetate as eluent. The Z isomer was crytalised using DCM/EtOH in indole and EtOH in case of imidazole.

Reference： [1]Gupta, Sahaj; Agarwal, Piyush K.; Saifuddin, Mohammad; Kundu, Bijoy [Tetrahedron Letters, 2011, vol. 52, # 44, p. 5752 - 5757]

37
[ 886-66-8 ]
[ 539-03-7 ]
[ 1340595-31-4 ]

Yield	Reaction Conditions	Operation in experiment
35%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In dimethyl sulfoxide at 100℃; for 16h; diastereoselective reaction;	General procedure: To a stirred solution of indole (1.0 mmol)/Imidazole (1.2 mmol) in DMSO was added 1,3-diyne (1.0 mmol), CuI (0.1 mmol), 1,10-phenanthroline (0.05 mmol) and cesium carbonate (1.5 mmol). The reaction mixture was heated at 100 °C for 5-16 h and the completion of the reaction was monitored by TLC. After completion of the reaction, it was cooled down to room temperature and then diluted with H2O (5 mL) followed by extraction of the product with EtOAc (3 × 10 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and the solvent was removed in vacuo. The crude product was purified on a silica gel column using hexane: ethyl acetate as eluent. The Z isomer was crytalised using DCM/EtOH in indole and EtOH in case of imidazole.

Reference： [1]Gupta, Sahaj; Agarwal, Piyush K.; Saifuddin, Mohammad; Kundu, Bijoy [Tetrahedron Letters, 2011, vol. 52, # 44, p. 5752 - 5757]

38
[ 288-47-1 ]
[ 536-74-3 ]
[ 35070-01-0 ]
[ 886-66-8 ]
[ 1263057-86-8 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 5381 - 5388

39
[ 274-47-5 ]
[ 536-74-3 ]
[ 886-66-8 ]
[ 1379574-67-0 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 5381 - 5388

40
[ 886-66-8 ]
[ 5392-10-9 ]
[ 1395726-61-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 2-bromo-4,5-dimethoxybenzaldehyde With <i>tert</i>-butylamine In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere; Stage #2: 1,4-diphenyl-1,3-butadiyne With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; lithium chloride In N,N-dimethyl-formamide at 120℃; for 25h; Inert atmosphere;	4.2. General annulation procedure for preparation of 4-phenyl-3-phenylethynyl-isoquinolines 3a-o General procedure: To a stirred solution of 2-bromobenzaldehydes 6a-d (1 mmol) in DMF (5 mL) was added tert-butylamine (1.5 mmol) and the reaction mixture was allowed to stirr under a nitrogen atmosphere at 100 °C for 1 h. This was followed by the sequential addition of the Pd(PPh3)4 (0.05 mmol), K2CO3 (2 mmol), LiCl (1 mmol), and the bis alkynes 2a-d (1.2 mmol) to the reaction mixture and was left for stirring at 120 °C for indicated time (Table 2). The reaction was monitored by TLC to establish completion and the reaction mixture, was cooled to room temperature and passed through bed of Celite, and filtrate was diluted with EtOAc (100 mL) and washed with saturated NH4Cl (50 mL) and brine solution (100 mL). The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product so obtained was purified by column chromatography by using EtOAc/hexane as eluent to afford 3.

Reference： [1]Location in patent: experimental part Mandadapu, Anil K.; Dathi, Meena D.; Arigela, Rajesh K.; Kundu, Bijoy [Tetrahedron, 2012, vol. 68, # 39, p. 8207 - 8215]

41
[ 886-66-8 ]
[ 94569-84-3 ]
[ 1395726-85-8 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: 2-bromo-5-fluorobenzaldehyde With <i>tert</i>-butylamine In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere; Stage #2: 1,4-diphenyl-1,3-butadiyne With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; lithium chloride In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;	4.2. General annulation procedure for preparation of 4-phenyl-3-phenylethynyl-isoquinolines 3a-o General procedure: To a stirred solution of 2-bromobenzaldehydes 6a-d (1 mmol) in DMF (5 mL) was added tert-butylamine (1.5 mmol) and the reaction mixture was allowed to stirr under a nitrogen atmosphere at 100 °C for 1 h. This was followed by the sequential addition of the Pd(PPh3)4 (0.05 mmol), K2CO3 (2 mmol), LiCl (1 mmol), and the bis alkynes 2a-d (1.2 mmol) to the reaction mixture and was left for stirring at 120 °C for indicated time (Table 2). The reaction was monitored by TLC to establish completion and the reaction mixture, was cooled to room temperature and passed through bed of Celite, and filtrate was diluted with EtOAc (100 mL) and washed with saturated NH4Cl (50 mL) and brine solution (100 mL). The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product so obtained was purified by column chromatography by using EtOAc/hexane as eluent to afford 3.

Reference： [1]Location in patent: experimental part Mandadapu, Anil K.; Dathi, Meena D.; Arigela, Rajesh K.; Kundu, Bijoy [Tetrahedron, 2012, vol. 68, # 39, p. 8207 - 8215]

42
[ 7436-90-0 ]
[ 14900-39-1 ]
[ 886-66-8 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 5678 - 5683

43
[ 886-66-8 ]
sodium triisopropylsilanethiolate [ No CAS ]
[ 1445-78-9 ]

Reference： [1]Synthesis,2013,vol. 45,p. 1713 - 1718

44
[ 886-66-8 ]
sodium triisopropylsilanethiolate [ No CAS ]
[ 1445-78-9 ]
[ 1426938-81-9 ]

Reference： [1]Synthesis,2013,vol. 45,p. 1713 - 1718
[2]Synthesis,2013,vol. 45,p. 1713 - 1718

45
[ 61613-20-5 ]
[ 536-74-3 ]
[ 886-66-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With palladium 10% on activated carbon; triethylamine; triphenylphosphine In water; N,N-dimethyl-formamide at 110℃; for 3h; Inert atmosphere;	General procedure for the synthesis of 2-substituted indoles General procedure: 2-Iodoanilide1 (1mmol),phenyl acetylene 2 (1.05 mmol), PPh3 (0.25 mmol), 10% Pd/C (5 mol %) and ZnCl2 (10mol %) containing 27-30 mol% of water were taken together in a two necked round bottomed flask fitted with condenser. After making the system inert under argon atmosphere, 7 equiv Et3N and DMF (6 mL) were added and the reaction mixture was stirred at 110°C. The progress of the reaction was monitored by TLC. Upon completionof the reaction, the mixture was allowed to cool to r.t, diluted with water and then extracted with EtOAc (3 x 20 mL). Then the organic layer was dried over Na2SO4 and concentrated in vacuum to get crude product which was then purified through column chromatography by using silica gel ( 60-120 mesh) and pet erther : EtOAc (5:1) aseluent.

Reference： [1]Ahmed, Atiur; Ghosh, Munmun; Sarkar, Pompy; Ray, Jayanta K. [Tetrahedron Letters, 2013, vol. 54, # 49, p. 6691 - 6694]

46
[ 10531-80-3 ]
[ 637-44-5 ]
[ 886-66-8 ]
6-methyl-2-(phenylethynyl)benzo[d]oxazole [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 7902 - 7906

47
[ 932-88-7 ]
[ 35692-27-4 ]
[ 7380-78-1 ]
[ 886-66-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 39% 2: 33 %Chromat.	With silver fluoride; potassium hydrogencarbonate; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In acetonitrile at 20℃; for 12h;	Synthesis of internal alkynes (3-12); general procedure General procedure: Alkynyl halide 1 (0.2 mmol), aryltrialkoxysilane 2 (0.4 mmol), Pd(dba)2 (3 mol %), AgF (3 equiv.), KHCO3 (2 equiv.), all values compared to 1, and MeCN (2 mL) were added to a Schlenk tube in turn. Then the solution was stirred at room temperature for the indicated time (usually 12 h) until complete consumption of starting material as monitored by TLC and GC-MS analysis. Afterthe reaction was finished, the crude reaction mixture was filtered, poured into diethyl ether (10 mL), washed with brine (3 mL × 3), extracted with diethyl ether (5 mL × 3), dried over anhydrous Na2SO4, and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate) to afford the desired product.

Reference： [1]Tang, Jiansheng; Guo, Cancheng [Journal of Chemical Research, 2014, vol. 38, # 2, p. 123 - 127]

48
[ 886-66-8 ]
[ 114-83-0 ]
N-(3-phenyl-2-(phenylethynyl)-1H-indol-1-yl)acetamide [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 16,p. 6176 - 6179

49
[ 616-43-3 ]
[ 886-66-8 ]
3-methyl-4,7-diphenyl-1H-indole [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 1463 - 1467

50
[ 886-66-8 ]
[ 128742-76-7 ]
methyl 9-methyl-5,8-diphenyl-9H-carbazole-3-carboxylate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 1463 - 1467

51
[ 650600-16-1 ]
[ 536-74-3 ]
[ 1008-75-9 ]
[ 886-66-8 ]
[ 1616956-25-2 ]
[ 81022-98-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 30% 2: 59% 3: 16% 4: 1%	With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); Selectfluor; triethylamine In water; acetonitrile at 20℃; for 19h; Inert atmosphere;
1: 50% 2: 20% 3: 18% 4: 27%	With potassium phosphate; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); Selectfluor In water; acetonitrile at 20℃; for 17h; Inert atmosphere;	Representative Procedure for the Synthesis of 3-Methyl-5-phenyl-4-phenylethynylisoxazole (4a). 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.
1: 22% 2: 25% 3: 46% 4: 15%	With potassium phosphate; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); Selectfluor; silver(I) triflimide In water; acetonitrile at 20℃; for 18h; Inert atmosphere;

1: 43% 2: 16% 3: 21% 4: 8%

With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); potassium carbonate; Selectfluor In water; acetonitrile at 20℃; for 27h; Inert atmosphere;

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

52
[ 28164-29-6 ]
[ 536-74-3 ]
[ 1008-75-9 ]
[ 886-66-8 ]
[ 1616956-25-2 ]
[ 81022-98-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 28% 2: 6% 3: 31% 4: 2%	With potassium phosphate; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); Selectfluor In water; acetonitrile at 20℃; for 72h; Inert atmosphere;

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

53
[ 613-91-2 ]
[ 108-24-7 ]
[ 536-74-3 ]
[ 886-66-8 ]
[ 57957-24-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 96% 2: 82%	With pyridine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In 1,2-dichloro-ethane at 120℃; for 5h; Inert atmosphere; Green chemistry;	2.2. General procedure for synthesis of enamide 3a and1,3-diyne 4a A 25 mL round-bottomed flask charged with ketoxime 1a(67.5 mg, 0.5 mmol), phenylacetylene 2a (102.0 mg, 1.0 mmol),acetic anhydride (102.0 mg, 1.0 mmol), pyridine (47.4 mg, 0.6mmol), CuI (9.5 mg, 10 mol%), and Pd(PPh3)2Cl2 (0.7 mg, 0.2mol%) in 1,2-dichloroethane (5.0 mL) was stirred at 120 °C for5 h under Ar. After completion of the reaction (detected usingthin-layer chromatography), the reaction mixture was cooledto room temperature, diluted with EtOAc (10 mL), and washedwith H2O (10 mL), brine (10 mL), and CuSO4 (2 mol/L, 5 mL).The organic layers were dried over anhydrous Na2SO4 andevaporated in vacuo. The residue was purified by chromatographyon silica gel to afford enamide 3a (77.3 mg, 96% yield)and 1,3-diyne 4a (82.8 mg, 82% yield).2.3. Analytical data for enamides 3 and 1,3-diynes 4N-(1-Phenylvinyl)acetamide (3a). 1H NMR (400 MHz, CDCl3)δ 7.39-7.34 (m, 6H), 5.78 (s, 1H), 5.07 (s, 1H), 2.04 (s, 3H). 13CNMR (100 MHz, CDCl3) δ 169.4, 140.5, 138.2, 128.5, 126.0,102.6, 24.3.
1: 85% 2: 30%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In 1,2-dichloro-ethane at 120℃; for 5h; Inert atmosphere; Green chemistry;	2.2. General procedure for synthesis of enamide 3a and1,3-diyne 4a A 25 mL round-bottomed flask charged with ketoxime 1a(67.5 mg, 0.5 mmol), phenylacetylene 2a (102.0 mg, 1.0 mmol),acetic anhydride (102.0 mg, 1.0 mmol), pyridine (47.4 mg, 0.6mmol), CuI (9.5 mg, 10 mol%), and Pd(PPh3)2Cl2 (0.7 mg, 0.2mol%) in 1,2-dichloroethane (5.0 mL) was stirred at 120 °C for5 h under Ar. After completion of the reaction (detected usingthin-layer chromatography), the reaction mixture was cooledto room temperature, diluted with EtOAc (10 mL), and washedwith H2O (10 mL), brine (10 mL), and CuSO4 (2 mol/L, 5 mL).The organic layers were dried over anhydrous Na2SO4 andevaporated in vacuo. The residue was purified by chromatographyon silica gel to afford enamide 3a (77.3 mg, 96% yield)and 1,3-diyne 4a (82.8 mg, 82% yield).2.3. Analytical data for enamides 3 and 1,3-diynes 4N-(1-Phenylvinyl)acetamide (3a). 1H NMR (400 MHz, CDCl3)δ 7.39-7.34 (m, 6H), 5.78 (s, 1H), 5.07 (s, 1H), 2.04 (s, 3H). 13CNMR (100 MHz, CDCl3) δ 169.4, 140.5, 138.2, 128.5, 126.0,102.6, 24.3.

Reference： [1]Liang, Hao; Ren, Zhihui; Wang, Yaoyu; Guan, Zhenghui [Cuihua Xuebao/Chinese Journal of Catalysis, 2015, vol. 36, # 1, p. 113 - 118]
[2]Liang, Hao; Ren, Zhihui; Wang, Yaoyu; Guan, Zhenghui [Cuihua Xuebao/Chinese Journal of Catalysis, 2015, vol. 36, # 1, p. 113 - 118]

54
[ 886-66-8 ]
[ 5042-30-8 ]
5-benzyl-3-phenyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In dimethyl sulfoxide; at 110℃; for 20h;Sealed tube;	General procedure: A reaction flask was charged with a mixture of symmetrical 1,3-di-alkyne 1 (0.4 mmol), methylhydrazine sulfate (4.0 equiv, 231 mg),Et2NH (3.2 mmol, 234 mg), and DMSO (5.0 mL). The flask con-taining the reaction mixture was sealed and the mixture was stirredat 110 C for 20 h, and then was cooled to r.t. H2O (10 mL) was add-ed to the resultant mixture. The product was extracted with EtOAc(3 10 mL), the combined organic layers were washed with brine(2 10 mL), and dried (Na2SO4). The solvent was removed underreduced pressure, and the residue obtained was purified via silicage l chromatography (eluent: PE-EtOAc, 10:1) to afford the desired1,3,5-trisubstituted pyrazole 2 (Table 2).

Reference： [1]Synthesis,2014,vol. 46,p. 2422 - 2429

55
[ 886-66-8 ]
[ 353-07-1 ]
3-(5-benzyl-3-phenyl-1H-pyrazol-1-yl)propanenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	In dimethyl sulfoxide; at 110℃; for 20h;Sealed tube;	General procedure: A reaction flask was charged with a mixture of symmetrical 1,3-di-alkyne 1 (0.4 mmol), methylhydrazine sulfate (4.0 equiv, 231 mg),Et2NH (3.2 mmol, 234 mg), and DMSO (5.0 mL). The flask con-taining the reaction mixture was sealed and the mixture was stirredat 110 C for 20 h, and then was cooled to r.t. H2O (10 mL) was add-ed to the resultant mixture. The product was extracted with EtOAc(3 10 mL), the combined organic layers were washed with brine(2 10 mL), and dried (Na2SO4). The solvent was removed underreduced pressure, and the residue obtained was purified via silicage l chromatography (eluent: PE-EtOAc, 10:1) to afford the desired1,3,5-trisubstituted pyrazole 2 (Table 2).

Reference： [1]Synthesis,2014,vol. 46,p. 2422 - 2429

56
[ 886-66-8 ]
[ 20570-96-1 ]
1,5-dibenzyl-3-phenyl-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With diethylamine; In dimethyl sulfoxide; at 110℃; for 20h;Sealed tube;	General procedure: A reaction flask was charged with a mixture of symmetrical 1,3-di-alkyne 1 (0.4 mmol), methylhydrazine sulfate (4.0 equiv, 231 mg),Et2NH (3.2 mmol, 234 mg), and DMSO (5.0 mL). The flask con-taining the reaction mixture was sealed and the mixture was stirredat 110 C for 20 h, and then was cooled to r.t. H2O (10 mL) was add-ed to the resultant mixture. The product was extracted with EtOAc(3 10 mL), the combined organic layers were washed with brine(2 10 mL), and dried (Na2SO4). The solvent was removed underreduced pressure, and the residue obtained was purified via silicage l chromatography (eluent: PE-EtOAc, 10:1) to afford the desired1,3,5-trisubstituted pyrazole 2 (Table 2).

Reference： [1]Synthesis,2014,vol. 46,p. 2422 - 2429

57
[ 14235-81-5 ]
[ 536-74-3 ]
[ 886-66-8 ]
[ 30405-78-8 ]
4-(phenylbuta-1,3-diyn-1-yl)aniline [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 12348 - 12351

58
[ 626-35-7 ]
[ 536-74-3 ]
[ 7063-99-2 ]
[ 886-66-8 ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 4643 - 4655

59
[ 79-24-3 ]
[ 536-74-3 ]
[ 25388-20-9 ]
[ 1008-75-9 ]
[ 886-66-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 33% 2: 14% 3: < 5 %Spectr.	With N-methylcyclohexylamine; copper diacetate In chloroform at 60℃; for 96h; Sealed tube;

Reference： [1]Baglieri, Ausilia; Meschisi, Luca; De Sarlo, Francesco; Machetti, Fabrizio [European Journal of Organic Chemistry, 2016, vol. 2016, # 27, p. 4643 - 4655]

60
[ 13688-68-1 ]
[ 886-66-8 ]
[ 1288982-13-7 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 1361 - 1364
Angew. Chem.,2016,vol. 129,p. 1381 - 1384,4

61
[ 2579-22-8 ]
[ 3112-88-7 ]
[ 886-66-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: Phenylpropargyl aldehyde; Benzyl phenyl sulfone With diethyl chlorophosphate In tetrahydrofuran at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; Inert atmosphere;	1 Example 1: Under a nitrogen atmosphere, 1 mmol of compound a1 and 1.2 mmol of compound b1 were mixed and dissolved in anhydrous tetrahydrofuranRan solution, 1 mmol of diethyl chlorophosphate was added and the reaction system was placed in an ice-water bath and stirred for 5 min.Bis (trimethylsilyl) amino lithium. The reaction was carried out overnight at room temperature, saturated ammonium chloride solution was added, extracted with dichloromethane, and saturated with chlorineSodium chloride solution, dried over anhydrous magnesium sulfate, filtered and the solvent was removed. Column chromatography gave the title compound A in 86% yield.

Reference： [1]Current Patent Assignee: NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN106366065, 2017, A Location in patent: Paragraph 0021; 0022; 0023; 0024; 0025; 0026; 0027; 0028

62
[ 2740-83-2 ]
[ 886-66-8 ]
3,6-diphenyl-2-[3-(trifluoromethyl)phenyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 10h;	General procedure: 1,4-Disubstituted-1,3-diacetylene (0.25 mmol) and K2CO3 (0.5 mmol) were added, under air, toa solution of appropriate benzylamine (2.0 mmol) in DMSO (0.5 mL) previously heated at 140 C.The resulting solution was stirred for 10 h at this temperature and washed with saturated aqNaCl,extracted with ethyl acetate (3 15 mL). The combined organic phase was dried with anhydrousNa2SO4, filtrated and concentrated under vacuum to yield the crude product. The crude product waspurified by thin layer chromatography on silica gel with petroleum ether as eluent.

Reference： [1]Molecules,2017,vol. 22

63
[ 88-82-4 ]
[ 536-74-3 ]
[ 886-66-8 ]
3-phenyl-5,7-diiodoisocoumarin [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 6131 - 6136

64
[ 886-66-8 ]
[ 150-61-8 ]
E,E-1,4,5,8,9,12-hexaphenyl-5,8-diazadodeca-3,9-diene-1,11-diyne [ No CAS ]
(Z,Z)-1,4,5,8,9,12-hexaphenyl-5,8-diazadodeca-3,9-diene-1,11-diyne [ No CAS ]
E,Z-1,4,5,8,9,12-hexaphenyl-5,8-diazadodeca-3,9-diene-1,11-diyne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With [(tetrahydrofuran)₃K₂{1,2-(PhN)₂C₂H₄}]; [(tetrahydrofuran)₅Ca₂{1,2-(PhN)₂C₂H₄}₂] In toluene at 20℃; Inert atmosphere; Schlenk technique; regioselective reaction;

Reference： [1]Ziemann, Steffen; Krieck, Sven; Görls, Helmar; Westerhausen, Matthias [Organometallics, 2018, vol. 37, # 6, p. 924 - 933]

65
[ 536-74-3 ]
[ 75-05-8 ]
[ 1912-16-9 ]
[ 109812-50-2 ]
[ 886-66-8 ]
[ 1165-53-3 ]

Yield	Reaction Conditions	Operation in experiment
	With [(pentamethylcyclopentadienyl)Co(indenyl)]; zinc at 80℃; for 3h; Inert atmosphere;

Reference： [1]Morales-Verdejo, Cesar; Camarada, María Belén; Morales, Verónica; Cañete, Álvaro; Martínez, Iván; Manriquez, Juan Manuel; Chávez, Ivonne [Journal of the Chilean Chemical Society, 2018, vol. 63, # 1, p. 3898 - 3901]

66
[ 886-66-8 ]
[ 3994-50-1 ]
(E)-5-(1,4-diphenylbut-1-en-3-yn-2-yl)-1-methyl-4-nitro-1H-pyrazole [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 2645 - 2650

67
[ 886-66-8 ]
[ 393-11-3 ]
1-(4-nitro-3-(trifluoromethyl)phenyl)-2,5-diphenyl-1H-pyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With copper(l) chloride; In N,N-dimethyl-formamide; for 48h;Reflux; Inert atmosphere;	General procedure: The monomers were synthesized using the procedure reported previously by some authors [19,21,23]. A mixture of precursor (0.50 g, 2.47 mmol), CuCl (I)(0.04 g, 0.49 mmol) and the appropriate amine (4.94 mmol), in DMF(10 ml), was refluxed under a nitrogen atmosphere for 48 h at 153 C in an oil bath, then allowed to cool at room temperature. The solvent was removed in vacuum and the product was purified bycolumn chromatography using hexane or a hexane-acetone mixture as eluent.

Reference： [1]Journal of Molecular Structure,2018,vol. 1171,p. 45 - 53

68
[ 886-66-8 ]
[ 121-01-7 ]
1-(4-nitro-2-(trifluoromethyl)phenyl)-2,5-diphenyl-1H-pyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With copper(l) chloride; In N,N-dimethyl-formamide; for 48h;Reflux; Inert atmosphere;	General procedure: The monomers were synthesized using the procedure reported previously by some authors [19,21,23]. A mixture of precursor (0.50 g, 2.47 mmol), CuCl (I)(0.04 g, 0.49 mmol) and the appropriate amine (4.94 mmol), in DMF(10 ml), was refluxed under a nitrogen atmosphere for 48 h at 153 C in an oil bath, then allowed to cool at room temperature. The solvent was removed in vacuum and the product was purified bycolumn chromatography using hexane or a hexane-acetone mixture as eluent.

Reference： [1]Journal of Molecular Structure,2018,vol. 1171,p. 45 - 53

69
[ 4771-47-5 ]
[ 536-74-3 ]
[ 886-66-8 ]
1-chloro-2-nitro-3-(phenylethynyl)benzene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 8556 - 8566

70
[ 394-01-4 ]
[ 536-74-3 ]
[ 1037492-79-7 ]
[ 886-66-8 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 8556 - 8566

71
[ 6280-88-2 ]
[ 536-74-3 ]
[ 886-66-8 ]
4-chloro-2-nitro-1-(phenylethynyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 65% 2: 64%	With 1,10-Phenanthroline; oxygen; sodium hydrogencarbonate; copper(II) sulfate In N,N-dimethyl-formamide; toluene at 150℃; for 24h; Molecular sieve; Schlenk technique;

Reference： [1]Yu, Yongqi; Chen, Xiang; Wu, Qianlong; Liu, Da; Hu, Liang; Yu, Lin; Tan, Ze; Gui, Qingwen; Zhu, Gangguo [Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 8556 - 8566]

72
[ 33844-21-2 ]
[ 536-74-3 ]
[ 886-66-8 ]
4-methoxy-2-nitro-1-(2-phenylethynyl)benzene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 8556 - 8566

73
[ 320-94-5 ]
[ 536-74-3 ]
[ 886-66-8 ]
2-nitro-1-(phenylethynyl)-4-(trifluoromethyl)benzene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 8556 - 8566

74
[ 13506-76-8 ]
[ 536-74-3 ]
[ 886-66-8 ]
1-methyl-3-nitro-2-(phenylethynyl)benzene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 8556 - 8566

75
[ 886-66-8 ]
[ 4271-96-9 ]
N-(2-(3,6-diphenylpyridin-2-yl)ethyl)-N-methylacetamide [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2638 - 2643

76
[ 24566-95-8 ]
[ 886-66-8 ]
1-(2-(3, 6-diphenylpyridin-2-yl)ethyl)azepan-2-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2638 - 2643

77
[ 18364-47-1 ]
[ 13755-29-8 ]
ammonium tetrafluoroborate [ No CAS ]
[ 886-66-8 ]
[ 107-06-2 ]
1-methyl-2,4-diphenyl-1H-pyrido[3,2,1-de][1,5]naphthyridin-7-ium tetrafluoroborate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 254 - 258
Angew. Chem.,2019,vol. 131,p. 260 - 264,5

78
[ 1456-22-0 ]
[ 886-66-8 ]
3-phenyl-4-(phenylethynyl)isoquinolin-1-amine [ No CAS ]