[ CAS No. 18282-51-4 ] {[proInfo.proName]}

Name: 18282-51-4|(4-Iodophenyl)methanol|98%
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Quality Control of [ 18282-51-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 18282-51-4 ]

Product Details of [ 18282-51-4 ]

CAS No. :	18282-51-4	MDL No. :	MFCD01732720
Formula :	C₇H₇IO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CNQRHSZYVFYOIE-UHFFFAOYSA-N
M.W :	234.03	Pubchem ID :	29012
Synonyms :

Calculated chemistry of [ 18282-51-4 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.29
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
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) :	-6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.01
Log Po/w (XLOGP3) :	1.87
Log Po/w (WLOGP) :	1.63
Log Po/w (MLOGP) :	2.46
Log Po/w (SILICOS-IT) :	2.66
Consensus Log Po/w :	2.13

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.9
Solubility :	0.297 mg/ml ; 0.00127 mol/l
Class :	Soluble
Log S (Ali) :	-1.92
Solubility :	2.84 mg/ml ; 0.0121 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.18
Solubility :	0.153 mg/ml ; 0.000655 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.57

Safety of [ 18282-51-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 18282-51-4 ]

* 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 [ 18282-51-4 ]
Downstream synthetic route of [ 18282-51-4 ]

[ 18282-51-4 ] Synthesis Path-Upstream 1~15

1
[ 74-85-1 ]
[ 18282-51-4 ]
[ 1074-61-9 ]

Reference： [1] Synlett, 2011, # 18, p. 2643 - 2647
[2] ChemCatChem, 2013, vol. 5, # 1, p. 159 - 172

2
[ 60-12-8 ]
[ 18282-51-4 ]
[ 52914-23-5 ]
[ 100-52-7 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986, vol. 25, p. 1004 - 1005

3
[ 50-00-0 ]
[ 18282-51-4 ]
[ 2351-50-0 ]

Reference： [1] Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 5-6, p. 619 - 632

4
[ 119072-55-8 ]
[ 18282-51-4 ]
[ 874-89-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With copper (II) trifluoroacetate hydrate; palladium diacetate In dimethyl sulfoxide at 130℃; for 6 h; Sealed tube; Inert atmosphere	General procedure: Aryl iodide (0.7 mmol, 1 equiv), tert-butyl isocyanide (2.1 mmol, 237 μL, 3 equiv), Pd(OAc)₂ (0.035 mmol, 8 mg, 5 mol percent), Cu(TFA)₂*xH₂O (1.4 mmol, 405 mg, 2 equiv) and DMSO (2.5 mL) were added to a 15 mL sealed tube, and stirred at 130 °C for 4-12 h under nitrogen. After completion of the reaction indicated by TLC, the mixture was extracted with Et₂O (510 mL). The combined organic phases was dried over Na₂SO₄, and concentrated under vacuum. Then the residue was purified by column chromatography on silica gel using petroleum ether (30-60 °C)/Et₂O as eluant to provide the pure target product.

Reference： [1] Tetrahedron, 2015, vol. 71, # 29, p. 4883 - 4887

5
[ 18282-51-4 ]
[ 16004-15-2 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1648 - 1655
[2] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2155 - 2165
[4] Journal of Organic Chemistry, 1995, vol. 60, # 3, p. 523 - 528
[5] Medicinal Chemistry Research, 1995, vol. 5, # 8, p. 618 - 630
[6] Chemistry - A European Journal, 2009, vol. 15, # 10, p. 2278 - 2288
[7] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 9, p. 3187 - 3200
[8] Organic Letters, 2015, vol. 17, # 15, p. 3810 - 3813

6
[ 18282-51-4 ]
[ 54589-53-6 ]
[ 16004-15-2 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1648 - 1655

7
[ 18282-51-4 ]
[ 115-19-5 ]
[ 10602-04-7 ]

Reference： [1] Organic and Biomolecular Chemistry, 2008, vol. 6, # 22, p. 4102 - 4104

8
[ 18282-51-4 ]
[ 10602-04-7 ]

Reference： [1] Patent: WO2018/160967, 2018, A1,

9
[ 18282-51-4 ]
[ 39959-59-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 9, p. 3187 - 3200

10
[ 18282-51-4 ]
[ 108-98-5 ]
[ 6317-56-2 ]

Reference： [1] Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1664 - 1672

11
[ 18282-51-4 ]
[ 78712-43-3 ]

Reference： [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 1, p. 127 - 131[2] Angew. Chem., 2014, vol. 126, # 01, p. 5131 - 5135

12
[ 288-32-4 ]
[ 18282-51-4 ]
[ 86718-08-3 ]

Reference： [1] Journal of Organic Chemistry, 2009, vol. 74, # 5, p. 2200 - 2202

13
[ 18282-51-4 ]
[ 138500-85-3 ]

Reference： [1] Patent: EP2450354, 2012, A1,

14
[ 18282-51-4 ]
[ 1066-54-2 ]
[ 275386-60-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃;	A suspension of (4-iodophenyl)methanol (3.00 g, 13.64 mmol), ethynyltrimethylsilane (2.13 mL, 15.38 mmol), copper (_) iodide (122 mg, 0.64 mmol), bis(triphenylphosphine)palladium(II) dichloride (450 mg, 0.64 mmol), TEA (5.36 ml, 38.46 mmol) were stirred in THF (22 mL) at ambient temperature for overnight. The reaction solvent was evaporated under reduced pressure, and the residue was purified by column chromatography with hexane/ethyl acetate (20/1, v/v) to obtain the compound 53 (2.66 g, quant. yield): 1H NMR (400 MHz, CDCl3) _ 7.44 (d, J = 8.4 Hz, 2H), 7.26 (d, J = 8.5 Hz, 2H), 4.63 (s, 2H), 2.17 (bs, 1H), 0.25 (s, 9H); 13C NMR (100 MHz, CDCl3) _ 141.3, 132.2, 126.7, 122.4, 105.0, 94.3, 64.9, 0.1.

Reference： [1] Patent: WO2018/160967, 2018, A1, . Location in patent: Page/Page column 86
[2] Journal of the American Chemical Society, 2015, vol. 137, # 45, p. 14319 - 14328

15
[ 18282-51-4 ]
[ 73183-34-3 ]
[ 302348-51-2 ]

Reference： [1] Patent: EP2450354, 2012, A1, . Location in patent: Page/Page column 19-20

[ 18282-51-4 ] Synthesis Path-Downstream 1~52

1
[ 619-58-9 ]
[ 18282-51-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With borane-THF; In tetrahydrofuran; at -20 - 50℃; for 14h;Reflux;	A flame dried, 300-ml three-necked, round-bottomed flask equipped with a magnetic stirring bar was charged with 4-iodobenzoic acid 9 (10.0 g, 40.3 mmol) and THF (20.0 mL). To the solution were slowly added BH3·THF (1.06 M solution in THF, 60.0 mL, 63.6 mmol) at -20 C. After stirring for 12 h at 50 C, an additional portion of BH3·THF (1.06 M solution in THF, 60.0 mL, 63.6 mmol) was added at -20 C and the reaction mixture was refluxed for 2 h. The reaction was quenched with ice-H2O (100 mL) and K2CO3. The reaction mixture was concentrated under reduced pressure and the residue was extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on a short pad of silica gel (Hexanes/EtOAc, 10:1) to give the titled alcohol S-1 (9.90 g, quant) as a white solid. Its spectral data were identical with those reported1 ; IR (KBr) 3500-3000, 1483, 1400, 1005, 791 cm-1; 1H NMR (500 MHz, CDCl3) d 7.66 (2H, d, J = 8.0 Hz), 7.07 (2H, d, J = 8.0 Hz), 4.59 (2H, s), 2.11 (1H, s); 13C NMR (125 MHz, CDCl3) d 140.4, 137.5, 128.7, 92.9, 64.5.
97%	With borane; for 4h;	EXAMPLE 10: (E)-3- [4- (8, 8-Dimethyl-5-p-tolyl-7,8- dihydro-2-naphthylselanyl) phenyl] acrylic acid a. 2-(4-IODOPHENYL) ETHANOL 12.5 g (50.4 mmol) of 4-iodobenzoic acid are dissolved in 125 ml of. tetrahydrofuran, and 112 ml (122 mmol) of a 1M solution of borane in tetrahydrofuran are then added dropwise. The reaction medium is stirred for 4 hours, acidified with 2N hydrochloric acid solution and then extracted with ethyl acetate. A white solid is obtained (11.49 g ; yield = 97%).
91%		In the inert gas N2 atmosphere, after dehydration and deoxidation treatment to the reaction bottle after adding 4 - iodo benzoic acid (124.0 mg, 0.5 mmol, gun for adding [...] borane (290 mul, 2 mmol), reacting at room temperature 12 hours, the reaction out of the glove box, in order to have three methoxybenzene (84.09 mg, 0.5 mmol) as the internal standard, CDCl3 for dissolving, stirring 10 minutes, sampling, with nuclear magnetic resonance. Calculated 1 H and the yield is 99%. The product of nuclear magnetic data: The residue is added to the sample in 1 g silica gel, in order to 3 ml methanol as a solvent, 50 C lower reaction 3 h, the borate further hydrolysis alcohol, after the reaction, extracted with ethyl acetate three times, the combined organic layer, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, through the silica gel (100 - 200 mesh) column chromatography purification, ethyl acetate/hexane (1:5) mixture as the eluent, to obtain the pure primary alcohol, separation and the yield is 94%.

	In tetrahydrofuran; methanol; ethyl acetate;	i. 4-Iodobenzyl alcohol. To a solution of 4-iodobenzoic acid (22 g) in tetrahydrofuran (450 mL) was added borane dimethylsulfide complex (35.5 mL, 10M in tetrahydrofuran), and the solution was allowed to stir overnight. The reaction was quenched by addition of methanol, and the solvent was evaporated. The residue was dissolved in ethyl acetate and filtered. The solvent was evaporated to give a solid, which was recrystallized from ether to yield a white solid, which was chromatographed, eluding with ether, to give 4-iodobenzyl alcohol (15.1 g).
	In tetrahydrofuran;	Step A -- Preparation of p-iodobenzyl alcohol To a stirred solution of p-iodobenzoic acid (5 mmole) in a dry tetrahydrofuran (20 ml) at -70 is added a suspension of lithium aluminum hydride (10 mmole) in tetrahydrofuran (10 ml). The mixture is allowed to warm to 0 and stirred at 0 for 2 hours. The reaction mixture is then poured into a dilute hydrochloric acid -- ice mixture and extracted with ether. The ether extract is washed with dilute bicarbonate solution, washed, dried over sodium sulfate and concentrated to dryness. Chromatography of the residue on a silica gel gives p-iodobenzyl alcohol.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4323 - 4326
[2]Chemistry - A European Journal,2005,vol. 11,p. 69 - 80
[3]Chemical Communications,2011,vol. 47,p. 1788 - 1790
[4]Organic and Biomolecular Chemistry,2013,vol. 11,p. 923 - 928
[5]Organic Letters,2014,vol. 16,p. 2410 - 2413
[6]Organometallics,2014,vol. 33,p. 6544 - 6549
[7]Patent: WO2004/46096,2004,A2 .Location in patent: Page 40
[8]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4895 - 4900
[9]Patent: CN109574808,2019,A .Location in patent: Paragraph 0025
[10]Chemical Science,2019,vol. 10,p. 7433 - 7441
[11]Synthetic Communications,2009,vol. 39,p. 1640 - 1654
[12]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3187 - 3200
[13]Journal of Porphyrins and Phthalocyanines,2018,vol. 22,p. 944 - 952
[14]Acta Chemica Scandinavica (1947),1957,vol. 11,p. 491,493
[15]Journal of Organic Chemistry,2004,vol. 69,p. 7423 - 7427
[16]Journal of labelled compounds and radiopharmaceuticals,1994,vol. 34,p. 213 - 220
[17]Patent: US5521179,1996,A
[18]Patent: US4064236,1977,A
[19]Patent: CN109369696,2019,A
[20]Patent: CN109467498,2019,A
[21]Chemical Communications,2019,vol. 55,p. 1386 - 1389

2
[ 60-12-8 ]
[ 18282-51-4 ]
[ 52914-23-5 ]
[ 100-52-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 1004 - 1005

3
[ 18282-51-4 ]
[ 18162-48-6 ]
[ 147283-96-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 1.75h;	A 200-ml round-bottomed flask equipped with a magnetic stirring bar was charged with alcohol S-1 (9.90 g, 40.3 mmol), imidazole (5.49 g, 80.6 mmol), and DMF (40.3 mL). To the solution were added TBSCl (6.83 g, 45.3 mmol) at room temperature. After stirring for 75 min at the same temperature, an additional portion of TBSCl (1.02 g, 6.77 mmol) was added and stirring was continued for 30 min. The reaction mixture was diluted with ice-H2O and EtOAc. The aqueous phase was extracted with EtOAc. The combined organic extracts were washed with H2O and brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on a short pad of silica gel (Hexanes/EtOAc, 10:1) to give the silyl ether 10 (14.7 g, quant) as a white solid. Its spectral data were identical with those reported2 ; IR (KBr) 2928, 2855, 1474, 1258, 1005, 841 cm-1; 1H NMR (500 MHz, CDCl3) d 7.66 (2H, d, J = 8.0 Hz), 7.08 (2H, d, J = 8.0 Hz), 4.69 (2H, s), 0.95 (9H, s), 0.11 (6H, s); 13C NMR (125 MHz, CDCl3) d 141.1, 137.2, 128.0, 92.0, 64.3, 25.9, 18.4, -5.3.
87%	With 1H-imidazole; In N,N-dimethyl-formamide; at 45℃; for 2h;	Tert-butyl(4-iodobenzyloxy)dimethylsilane (3). To a solution of compound (2) (9 g, 38.5 mmol, 1.0 equiv), TBSCl (5.8 g, 38.5 mmol, 1.0 equiv) and imidazole (5.3 g, 77 mmol, 2.0 equiv) in DMF (18 mL) was stirred for 2 h at 45 C. The reaction mixture was diluted with CH2Cl2 (200 mL) and washed with water (200 mL x 3). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was dried under high vacuum overnight to produce the title compound (3) (11.6 g, 87 %). 1H NMR (300 MHz, d6-DMSO): 0.05 (s, 6H), 0.88 (s, 9H), 4.64 (s, 2H), 7.09-7.11 (d. 2H), 7.66-7.69 (d, 2H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4323 - 4326
[2]Journal of Organic Chemistry,2014,vol. 79,p. 2463 - 2472
[3]Journal of labelled compounds and radiopharmaceuticals,1994,vol. 34,p. 213 - 220
[4]Journal of Organic Chemistry,2007,vol. 72,p. 9003 - 9009
[5]Patent: WO2008/154642,2008,A2 .Location in patent: Page/Page column 126
[6]Organic Letters,2019,vol. 21,p. 7380 - 7385
[7]Organic Letters,2005,vol. 7,p. 5199 - 5202

4
[ 1711-02-0 ]
[ 18282-51-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium tetrahydroborate In 1,4-dioxane at 100℃; for 0.166667h;
	With sodium tetrahydroborate; lithium chloride In 1,2-dimethoxyethane for 1h; Yield given;
	With sodium borohydrid In 1,4-dioxane; dichloromethane; water	4.III III. III. Nitrone Carboxylic Acid Synthesis (6d-7b-d): 4-Iodobenzyl alcohol. (Acheson, R. M.; Lee. G. C. M. J. Chem. Soc. Perkin Trans. I 1987, 2321-2332.) To a stirred suspension of sodium borohydride (5.68 g, 150 mmol, 2.0 equiv) in 50 mL dioxane at 0° C. was added dropwise a solution of 4-iodobenzoyl chloride (19.99 g, 75 mmol, 1.0 equiv) in 50 mL dioxane over 25 min. The resulting mixture was heated to 100° C. for 90 min under a reflux condenser then cooled to 0° C. 50 mL H2O was added cautiously under a flowing stream of nitrogen. [CAUTION: Evolves gas!] The mixture was extracted 3125 mL CH2Cl2 and the combined organic extracts were washed with 2H2O, 20.1N HCl, 21N NaOH, H2O, and brine, dried (MgSO4), filtered, and evaporated to yield 16.9 g of crude 4-iodobenzyl alcohol as a white solid, determined by NMR to contain 78% desired product with the remainder residual starting material and 4-iodobenzoic acid.

	With sodium tetrahydroborate In tetrahydrofuran
4.54 g	With sodium tetrahydroborate In 1,4-dioxane at 0 - 100℃; for 1.91667h;

Reference： [1]Mounetou, Emmanuelle; Debiton, Eric; Buchdahl, Catherine; Gardette, Daniel; Gramain, Jean-Claude; Maurizis, Jean-Claude; Veyre, Annie; Madelmont, Jean-Claude [Journal of Medicinal Chemistry, 1997, vol. 40, # 18, p. 2902 - 2909]
[2]Ekhato; Huang [Journal of labelled compounds and radiopharmaceuticals, 1994, vol. 34, # 3, p. 213 - 220]
[3]Current Patent Assignee: HARVARD UNIVERSITY - US6448443, 2002, B1
[4]Location in patent: scheme or table Mariaca, Raúl; Labat, Gaël; Behrnd, Norwid-Rasmus; Bonin, Michel; Helbling, Fabien; Eggli, Patrick; Couderc, Gaëtan; Neels, Antonia; Stoeckli-Evans, Helen; Hulliger, Jürg [Journal of Fluorine Chemistry, 2009, vol. 130, # 2, p. 175 - 196]
[5]Everson, Daniel A.; Shrestha, Ruja; Weix, Daniel J. [Journal of the American Chemical Society, 2010, vol. 132, # 3, p. 920 - 921]

5
[ 18282-51-4 ]
[ 124-63-0 ]
[ 199608-28-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In dichloromethane; at -40℃; for 0.5h;	General procedure: Each benzyl alcohol derivative (1.00 mmol) was combined with dichloromethane (5 mL) and triethylamine (280 mL, 2.01 mmol) in a50-mL round-bottom flask. The mixture was cooled to 40 C, and methanesulfonyl chloride (110 muL, 1.40 mmol) was added to the mixture while being stirred vigorously. After 30 min at 40 C, the reaction mixture was washed with a 1% HCl solution (3 10 mL) and a saturated aqueous NaHCO3 solution (3 x 5 mL). The organic layer was dried (Na2SO4), filtered and the solvent was removed in vacuo to produce high yields (90-100%) of pure benzyl mesylates 8a-i.
	With triethylamine; In dichloromethane; at -50℃;Inert atmosphere;	General procedure: Benzyl alcohol (1.08 g, 10.0 mmol) and anhydrousdichloromethane (DCM, 20 mL) were added to a 50 mLround-bottom flask under nitrogen atmosphere. The mixturewas cooled to -50 C and then triethylamine (2.78 mL,20.0 mmol) was added, followed by slow addition ofmethanesulfonyl chloride (Ms-Cl, 1.20 mL, 15.0 mmol).The progress of the reaction was monitored by TLC. Afterits completion, 20 mL of water were added. The layerswere separated and the organic layer was washed with1% m/v HCl aqueous solution (3 × 15 mL), followed byNaHCO3 saturated aqueous solution (3 × 5 mL), dried overMgSO4, and concentrated under reduced pressure. Thecompound 2a was obtained in 87% yield (1.63 g, 8.76 mmol)and it was not submitted to any further purificationprocedure.

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 859 - 864
[2]Journal of the Brazilian Chemical Society,2013,vol. 24,p. 953 - 961
[3]European Journal of Medicinal Chemistry,2014,vol. 84,p. 595 - 604
[4]Tetrahedron,1998,vol. 54,p. 9317 - 9332
[5]Green Chemistry,2017,vol. 19,p. 5054 - 5059
[6]European Journal of Medicinal Chemistry,2018,vol. 146,p. 274 - 286
[7]Mendeleev Communications,2018,vol. 28,p. 195 - 197
[8]Journal of the Brazilian Chemical Society,2019,vol. 30,p. 541 - 561

6
[ 18282-51-4 ]
[ 15164-44-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With dipyridinium dichromate; In dichloromethane; for 15h;	b. 4-IODOBENZALDEHYDE 11.49 g (49.1 mmol) of 2- (4-IODOPHENYL)- ethanol are dissolved in 375 ml of dichloromethane, and 37 g (98.2 mmol) of pyridinium dichromate are then added portionwise. The reaction medium is stirred for 15 hours, filtered through silica and eluted with dichloromethane. A yellow solid is obtained (10.4 g ; yield = 91%).
86%	With [ReOCl3(PPh3)2]; bis(4-chlorophenyl)sulfoxide; In toluene; for 17h;Reflux;	General procedure: To a solution of ReOCl3(PPh3)2 (0.083 g, 0.1 mmol) in toluene (3 mL) was added the bis(4-chlorophenyl) sulfoxide (0.271 g, 1 mmol) and the alcohol (1.0 mmol). The reaction mixture was heated at reflux temperature in air (the reaction times are indicated in Tables 1-4) and the progress of the reaction was monitored by TLC. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford carbonyl compounds and bis(4-chlorophenyl) sulfide, which are all known compounds and their 1H NMR and 13C NMR data are consistent with those of the commercial products.
85%	With C48H36Cu2N4O8S2; dihydrogen peroxide; In acetonitrile; at 80℃; under 760.051 Torr; for 2h;	General procedure: To a solution of benzyl alcohol derivative (Eq. (4)) (5 mmol), in 10 mL acetonitrile catalyst [Cu2(L)2(NO3)2] (0.002 mmol), and 50% H2O2 (5 mL) was added and the mixture was refluxed at 80 C for 2 h. The mixture was then poured into water and the product was extracted with dichloromethane and dried over Na2SO4. The solvent was removed and the product was purified by column chromatography. The product was characterized by IR and 1H NMR spectra.

85%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In n-heptane; at 80℃; under 760.051 Torr; for 24h;	General procedure: A mixture of catalyst PS-PEG-TD2-Cu(OAc)2 (100 mg, 0.05mmol Cu), BnOH (1a, 27.0 mg, 0.25 mmol), and TEMPO (7.8 mg,0.05 mmol) in heptane (2.0 mL) was stirred at 80 C for 24 hunder air (1 atm). The mixture was then cooled and filtered, andthe resulting solid material was washed with Et2O (3 × 2 mL).The organic phases were combined, concentrated to a volume of2 mL, and the internal standard was added to determine the GCyield. The crude product was purified by column chromatography[silica gel, hexane-Et2O (99:1)]. In the formation of somebenzaldehydes, low isolated yields were observed because ofinstability of the benzaldehydes on silica gel
82%	With C35H28Cl2N5PRu; potassium tert-butylate; In toluene; at 50℃; for 6h;	General procedure: using the complex 1 as catalyst in presence of a base following a general procedure. In a round-bottom flask, 1 mmol of substrate, 0.005mmol of catalyst (3.6mg) and 0.010 mmol of tBuOK (1.1mg) were mixed in 10mL toluene. The reaction mixture was heated at 50C in aerobic condition with continuous stirring for 6h and then the solvent was evaporated with a rotary evaporator under reduced pressure. The crude product, thus obtained, was purified on preparative silica gel GF-254 TLC plate using ethyl acetate: hexane (1:10) solvent mixture as eluent. The oxidized products were characterized by NMR spectroscopy (See Figs. S4-S32).
80%	With C36H27CuN8O2; dihydrogen peroxide; In acetonitrile; at 70℃; for 4h;	General procedure: A mixture of the aromatic alcohol (0.5 mmol), catalyst 4a (0.002 mmol) and 30% H2O2 (5 equiv.) was added to a roundbottom flask containing 10 mL of acetonitrile. The total mixture was stirred at 70 C for 4 h. The reaction was monitored by TLC. After completion of the reaction, the solvent was removed, theorganic phase was separated and dried over Na2SO4, and the product was purified by column chromatography (hexane/ethyl acetate).Yields were determined by weighing the isolated products, which were characterized by 1H NMR and IR spectroscopy (Table 5).
73%	With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; acetonitrile; at 20℃; for 2h;4 A molecular sieves;	A solution of 4-iodobenzyl alcohol (9g, 38. 29mmol) in dichloromethane (90mL) and acetonitrile (lOmL) was treated sequentially with 4 A molecular sieves powder (9g), tetra-n-propyl ammoniumperruthenate (0.13g) and N-methyl morpholine-N-oxide (9g, 76. 6mmol). After stirring at ambient temperature for 2h, the reaction mixture was diluted with hexane and subjected to flash column chromatography over silica gel (230-400mesh) using 6-10% ethyl acetate in hexane as the eluent to afford the title compound (2. 5g pure and 4g-95% pure, 73%). 'H NMR (300 MHz, CDCl3) : b 9.96 (s, 1H), 7.92 (d, 2H, J= 8. 5Hz), 7.59 (d, 2H, J= 8. 5Hz).
73%	With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; acetonitrile; at 20℃; for 2h;Molecular sieve;	4-Iodo-benzaldehyde; A solution of 4-iodobenzyl alcohol (9g, 38. 29mmol) in dichloromethane (90mL) and acetonitrile (lOmL) was treated sequentially with 4 A molecular sieves powder (9g), tetra-ra-propyl ammoniumperruthenate (0.13g) and N-methyl morpholine-N-oxide (9g, 76.6mmol). After stirring at ambient temperature for 2h, the reaction mixture was diluted with hexane and subjected to flash column chromatography over silica gel (230-400mesh) using 6-10% ethyl acetate in hexane as the eluent to afford the title compound (2. 5g pure and 4g-95% pure, 73%). 'H NMR (300 MHz, CDC13) : 8 9.96 (s, 1H), 7.92 (d, 2H, J= 8. 5Hz), 7.59 (d, 2H, J = 8. 5Hz).
88%Chromat.	With C49H43IrN2P2; potassium carbonate; In acetone; for 8h;	General procedure: In a typical run, an oven-dried round bottom flask was charged with a known mole percent of catalyst, K2CO3 (1.7mmol), primary or secondary alcohol (1.0mmol) in acetone medium (8mL). The mixture was stirred at 40C. After the specified time the reaction mixture was extracted with ether (4×10mL). The combined organic layer was washed with water (3×10mL), and dried over anhydrous Na2SO4. Solvent was removed under vacuum. The residue was dissolved in hexane and analyzed by GC-MS.
	With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water-d2; cyclomaltooctaose; at 60℃; for 0.5h;Green chemistry;	General procedure: To a clean and dry small vial, a solution of substrate 1 (15.0 mumol, 1.0 equivalent) was added using an aqueous cyclodextrin solution (1.0 mL) of the specified concentration in D2O. DBDMH 3 (4.3 mg, 15.0 mumol, 1.0 equivalent) was added to the reaction mixture and sonicated to make sure that the reagents were well suspended. The reaction mixture was heated at 60 C with occasional shaking to maintain the homogeneity of the solution. After the desired period of time, the 1H NMR spectrum of the reaction mixture was recorded to determine the percent conversion.
87%Chromat.	With potassium carbonate; In toluene; at 110℃; for 12h;	General procedure: Benzyl alcohol (108mg, 1.0mmol), AuSBA-15 (6wt%, 20mg) and K2CO3 (829mg, 6.0mmol) was dissoveled in toluene (6.0mL), the reaction mixture was stirred for 12hat 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 title compound.

Reference： [1]Chemistry - A European Journal,2005,vol. 11,p. 69 - 80
[2]RSC Advances,2014,vol. 4,p. 48777 - 48782
[3]Organic Process Research and Development,2019,vol. 23,p. 825 - 835
[4]Advanced Synthesis and Catalysis,2004,vol. 346,p. 767 - 776
[5]Synlett,2011,p. 2799 - 2802
[6]Advanced Synthesis and Catalysis,2019
[7]Advanced Synthesis and Catalysis,2019,vol. 361,p. 2262 - 2267
[8]RSC Advances,2014,vol. 4,p. 61907 - 61911
[9]Patent: WO2004/46096,2004,A2 .Location in patent: Page 40
[10]Journal of Chemical Research,2006,p. 263 - 266
[11]Catalysis Communications,2013,vol. 40,p. 134 - 138
[12]Inorganica Chimica Acta,2014,vol. 418,p. 171 - 179
[13]Synlett,2018,vol. 29,p. 1152 - 1156
[14]Inorganica Chimica Acta,2019,vol. 484,p. 160 - 166
[15]Polyhedron,2014,vol. 79,p. 43 - 51
[16]Chemistry - A European Journal,2016,vol. 22,p. 8814 - 8822
[17]Inorganic Chemistry,2018,vol. 57,p. 11995 - 12009
[18]Journal of Porphyrins and Phthalocyanines,2018,vol. 22,p. 944 - 952
[19]Patent: WO2005/58301,2005,A1 .Location in patent: Page/Page column 75-76
[20]Patent: WO2005/58798,2005,A2 .Location in patent: Page/Page column 47
[21]Chemistry - A European Journal,2015,vol. 21,p. 18779 - 18784
[22]Journal of the American Chemical Society,1999,vol. 121,p. 9073 - 9087
[23]Journal of Organic Chemistry,2004,vol. 69,p. 7423 - 7427
[24]Journal of the Chemical Society. Perkin Transactions 2 (2001),2002,p. 1151 - 1157
[25]Journal of Fluorine Chemistry,2009,vol. 130,p. 175 - 196
[26]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4940 - 4943
[27]Synthesis,2010,p. 3974 - 3976
[28]E-Journal of Chemistry,2011,vol. 8,p. 264 - 268
[29]Journal of Organometallic Chemistry,2014,vol. 751,p. 760 - 768
[30]Chinese Journal of Chemistry,2014,vol. 32,p. 405 - 409
[31]Dalton Transactions,2014,vol. 43,p. 12313 - 12320
[32]Green Chemistry,2014,vol. 16,p. 4524 - 4529
[33]European Journal of Inorganic Chemistry,2015,vol. 2015,p. 939 - 947
[34]Synthetic Communications,2016,vol. 46,p. 636 - 644
[35]Inorganic Chemistry,2016,vol. 55,p. 8160 - 8173
[36]Journal of Materials Chemistry A,2017,vol. 5,p. 17580 - 17588
[37]Journal of Organometallic Chemistry,2017,vol. 851,p. 46 - 51
[38]Journal of Catalysis,2017,vol. 354,p. 152 - 159
[39]Catalysis science and technology,2017,vol. 7,p. 4955 - 4963
[40]New Journal of Chemistry,2018,vol. 42,p. 654 - 661
[41]European Journal of Organic Chemistry,2019,vol. 2019,p. 3190 - 3194
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[43]Dalton Transactions,2020,vol. 49,p. 682 - 689
[44]Chemistry - A European Journal,2020

7
[ 89059-06-3 ]
[ 18282-51-4 ]
3-pyrrol-1-yl-propionic acid 4-iodo-benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃;

Reference： [1]Kashiwagi, Yoshitomo; Chiba, Shinya; Ikezoe, Hiroshi; Anzai, Jun-Ichi [Synlett, 2004, # 14, p. 2513 - 2516]

8
[ 18282-51-4 ]
[ 59528-27-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4895 - 4900

9
[ 15290-29-6 ]
[ 18282-51-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 95 percent / iodine monochloride / CCl₄ / 1.) RT, 30 min, 2.) reflux, 1 h 2: oxalyl chloride, DMF / toluene / 1 h / Ambient temperature 3: LiCl, NaBH₄ / 1,2-dimethoxy-ethane / 1 h

Reference： [1]Ekhato; Huang [Journal of labelled compounds and radiopharmaceuticals, 1994, vol. 34, # 3, p. 213 - 220]

10
[ 51934-41-9 ]
[ 18282-51-4 ]

Yield	Reaction Conditions	Operation in experiment
85%		A stirred, cooled (-78C) solution of ethyl-4-iodo-benzoate (available from Lancaster, 12.9g, 45mmol) in anhydrous dichloromethane (lOOmL) under argon was treated with a 1M solution of di-isobutyl aluminum hydride in dichloromethane (100mL, 100mmol). The reaction mixture was allowed to warm to 0C in l. 5h, quenched with saturated aqueous ammonium chloride solution and the resulting emulsion was filtered over a bed of celite. The phases in the filtrate were separated and the aqueous phase was extracted with dichloromethane (xl). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title product as a white solid (9g, 85%). 1H NMR (300 MHz, CDCl3) : 5 7.65 (d, 2H, J= 7.6Hz), 7.05 (d, 2H, J= 7.6Hz), 4.57 (s, 2H), 2.40 (br s, 1H).
85%		4-Iodo-benzyl alcohol; A stirred, cooled (-78C) solution of ethyl-4-iodo-benzoate (available from Lancaster, 12.9g, 45mmol) in anhydrous dichloromethane (lOOmL) under argon was treated with a 1M solution of di-isobutyl aluminum hydride in dichloromethane (lOOmL, lOOmmol). The reaction mixture was allowed to warm to 0C in 1. 5h, quenched with saturated aqueous ammonium chloride solution and the resulting emulsion was filtered over a bed of celite. The phases in the filtrate were separated and the aqueous phase was extracted with dichloromethane (xl). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title product as a white solid (9g, 85%). 'H NMR (300 MHz, CDCl3) : 8 7.65 (d, 2H, J= 7.6Hz), 7.05 (d, 2H, J= 7. 6Hz), 4.57 (s, 2H), 2.40 (br s, 1H).

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 2278 - 2288
[2]Chemistry - A European Journal,2015,vol. 21,p. 14737 - 14741
[3]Catalysis science and technology,2019,vol. 9,p. 6047 - 6058
[4]Synthetic Communications,2009,vol. 39,p. 1640 - 1654
[5]Patent: WO2005/58301,2005,A1 .Location in patent: Page/Page column 76
[6]Patent: WO2005/58798,2005,A2 .Location in patent: Page/Page column 47
[7]ChemSusChem,2020,vol. 13,p. 1800 - 1807

11
[ 18282-51-4 ]
[ 4214-79-3 ]
[ 210037-26-6 ]

Yield	Reaction Conditions	Operation in experiment
	With copper; potassium carbonate;	Step 1 5-Chloro-1-(4-hydroxymethyl-phenyl)-1H-pyridin-2-one <strong>[4214-79-3]5-Chloro-2-pyridinol</strong> (0.61 g, 4.7 mmol), 4-iodobenzyl-alcohol (1.00 g, 4.27 mmol), Copper (0.27 g, 4.27 mmol) and K2CO3 (0.65 g, 4.70 mmol) were heated at 180° C. for 16 hrs. The brown reaction mixture was cooled, diluted with EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (2*) and the combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc as eluent) to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD) delta 7.74 (d,J=2.7 Hz, 1H), 7.59 (dd, J=3.0 and 9.6 Hz, 1H), 7.51 (d, J=8.6 Hz, 2H), 7.37 (d, J=8.4 Hz, 2H), 6.61 (d, J=9.4 Hz, 1H) and 4.67(s,1H) ppm.

Reference： [1]Patent: US2003/220241,2003,A1

12
[ 18282-51-4 ]
[ 4214-79-3 ]
[ 584-08-7 ]
[ 210037-26-6 ]

Yield	Reaction Conditions	Operation in experiment
	With copper;	Step 1 5-Chloro-1-(4-hydroxymethyl-phenyl)-1H-pyridin-2-one <strong>[4214-79-3]5-Chloro-2-pyridinol</strong> (0.61 g, 4.7 mmol), 4-iodobenzyl-alcohol (1.00 g, 4.27 mmol), Copper (0.27 g, 4.27 mmol) and K2 CO3 (0.65 g, 4.70 mmol) were heated at 180° C. for 16 hrs. The brown reaction mixture was cooled, diluted with EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (2*) and the combined organic extracts were washed with brine, dried (Na2 SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc as eluent) to afford the title compound as a white solid. 1 H NMR (400 MHz, CD3 OD) delta 7.74 (d, J=2.7 Hz, 1H), 7.59 (dd, J=3.0 and 9.6 Hz, 1H), 7.51 (d, J=8.6 Hz, 2H), 7.37 (d, J=8.4 Hz, 2H), 6.61 (d, J=9.4 Hz, 1H) and 4.67(s,1H) ppm.

Reference： [1]Patent: US5939439,1999,A

13
[ 15164-44-0 ]
[ 18282-51-4 ]

Yield	Reaction Conditions	Operation in experiment
97%		(4-Iodophenyl)methanol (2). To a solution of compound (1) (50 g, 0.21 mol, 1.0 equiv) in methanol (500 mL) was added with NaBH4 (20.5 g, 0.5 mol, 2.5 equiv) slowly under 1OC for 1 h and stirred for 2 h. The reaction mixture was concentrated under reduced pressure, quenched with water (300 mL), and extracted with EtOAc (300 mL x 3). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was dried in vacuo overnight to provide the title compound (2) (49 g, 97%).
86%	With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; tris[3,5-bis(trifluoromethyl)phenyl]-borane; In 1,4-dioxane; at 25℃; for 12h;Glovebox;	General procedure: In a glovebox, aldehydes (0.25 mmol) and the Hantzsch ester 1 (95 mg, 0.38 mmol) were added to asolution of tris[3,5-bis(trifluoromethy)phenyl]borane (9) (8.1 mg, 12.5 mumol) in 1 mL of anhydrous1,4-dioxane. The reaction mixture was stirred at 25 or 100 C for 12 h. An internal standard (biphenylor mesitylene) was added to the reaction mixture and filtrated through a cotton plug. The resultingsolution was analyzed with gas chromatography.

Reference： [1]Organometallics,2013,vol. 32,p. 4501 - 4506
[2]Patent: WO2008/154642,2008,A2 .Location in patent: Page/Page column 126
[3]Catalysis Communications,2019,vol. 124,p. 32 - 35
[4]Synlett,2015,vol. 26,p. 2037 - 2041
[5]Journal of the American Chemical Society,2015,vol. 137,p. 14295 - 14304
[6]RSC Advances,2015,vol. 5,p. 102736 - 102740
[7]Chemical Communications,2017,vol. 53,p. 4215 - 4218
[8]Journal of the American Chemical Society,2017,vol. 139,p. 4901 - 4915

14
[ 288-32-4 ]
[ 18282-51-4 ]
[ 86718-08-3 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 2200 - 2202

15
[ 18282-51-4 ]
[ 108-98-5 ]
[ 6317-56-2 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 1664 - 1672

16
[ 18282-51-4 ]
[ 53339-53-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 4-iodo-benzyl alcohol With copper(l) iodide; potassium carbonate; sulfur In N,N-dimethyl-formamide at 90℃; for 12h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In N,N-dimethyl-formamide at 40℃; Inert atmosphere; Cooling with ice;

Reference： [1]Jiang, Yongwen; Qin, Yuxia; Xie, Siwei; Zhang, Xiaojing; Dong, Jinhua; Ma, Dawei [Organic Letters, 2009, vol. 11, # 22, p. 5250 - 5253]

17
[ 18282-51-4 ]
[ 1097731-47-9 ]
[ 1069130-83-1 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 9158 - 9164

18
[ 18282-51-4 ]
[ 589-15-1 ]
[ 1300746-81-9 ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: 4-iodo-benzyl alcohol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: 1-bromomethyl-4-bromobenzene With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere;
51%	Stage #1: 4-iodo-benzyl alcohol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-bromomethyl-4-bromobenzene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h;	To a stirred solution of 4-iodobenzyl alcohol (1 .33 g, 5.5 mmol, 1 .1 equiv) in DMF (40 mL) at 0 °C was added NaH (240 mg, 60% in mineral oil, 6.0 mmol, 1 .2 equiv), and the mixture was warmed to room temperature and stirred for 30 min. The mixture was cooled to 0 °C, and 4-bromobenzyl bromide (1 .25 g, 5.0 mmol, 1 .0 equiv) and tetra-n-butylammonium iodide (92.3 mg, 0.25 mmol, 0.050 equiv) were added. The reaction mixture was warmed to room temperature, stirred for 2 h and quenched with saturated aqueous NH4CI solution. The mixture was extracted with Et20, and the organic layer was washed with 1 M aqueous HCI solution and brine and dried over Na2S04. After evaporation of the solvent, the crude mixture was purified by flash silica gel column chromatography (hexane/Et20 = 400/1 to 20/1 ) to give 1-bromo-4-[(4-iodobenzyloxy)methyl]benzene (3v) as a white solid (1 .02 g, 51 % yield). 1H NMR (400 MHz, CDC ): δ 7.68 (d, / = 8.4 Hz, 2 H), 7.48 (d, / = 8.4 Hz, 2 H), 7.22 (d, / = 8.4 Hz, 2 H), 7.10 (d, / = 8.4 Hz, 2 H), 4.49 (s, 4 H). 13C{1 H} NMR (125 MHz, CDCI3): δ 137.9, 1 37.8, 137.2, 131 .8, 129.8, 129.6, 121 .9, 93.4, 71 .8, 71 .7. Anal, calcd. for C14H12BHO: C, 41 .72; H, 3.00; found: C, 41 .71 ; H, 2.77.

Reference： [1]Morimoto, Hiroyuki; Tsubogo, Tetsu; Litvinas, Nichole D.; Hartwig, John F. [Angewandte Chemie - International Edition, 2011, vol. 50, # 16, p. 3793 - 3798]
[2]Current Patent Assignee: UNIVERSITY OF ILLINOIS (SYSTEM) - WO2012/24564, 2012, A1 Location in patent: Page/Page column 24

19
[ 74-85-1 ]
[ 18282-51-4 ]
[ 1074-61-9 ]

Reference： [1]Synlett,2011,p. 2643 - 2647
[2]ChemCatChem,2013,vol. 5,p. 159 - 172

20
[ 18282-51-4 ]
[ 73183-34-3 ]
[ 302348-51-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl tert-butyl ether; XPhos; In ethanol; at 20℃; for 0.5h;	General procedure: Method (1): Synthesis from 4-tert-butylchlorobenzene as a raw material: K3P04 · 7H20 (3.0 g, 8.85 mmol) and bis-pinacol borate (749 mg, 2.95 mmol) were sequentially added to the reaction flask.The catalyst-chloro (2-dicyclohexyl phosphino-2 ', 4', 6'-tri - triisopropyl-1,1'-biphenyl) (1,1'-biphenyl -2-amino-2'_ -yl)palladium(II) (12 mg, 0.015 mmol) and ligand 2-dicyclohexylphosphine-2',4',6/-triisopropylbiphenyl (4 mg, 0.008 mmol), followed by EtOH (6 mL) The mixture was stirred, and p-tert-butylchlorobenzene (0.5 mL, 2.95 mmol) was added and the mixture was reacted at room temperature for 0.5 h. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (2 mL) After washing with ethyl acetate (6 mL) in three portions, the filtrate was combined, and the solvent was evaporated to dryness, and the solvent was separated by silica gel (200 to 300 mesh). The eluent was petroleum ether and ethyl acetate. 10~80:1), obtained as a white solid, identified by NMR spectrum as 4-tert-butylphenylboronic acid pinacol ester, yield 98%
	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 85℃; for 18h;Inert atmosphere;	(IV) Synthesis of Compound (12); (4-[{4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl}(4H-1,2,4-triazol-4-yl)amino]benzonitrile); <Method A>; Compound (12) was synthesized according to the scheme below.; Here, Compound (16) was synthesized according to the scheme below.; (i) Synthesis of Compound (14) (4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl alcohol) (see Non-patent Literature 14 (Filippis, A.; Morin, C.; Thimon, C., Synth. Commun. 2002, 32, 2669-2676)); Under argon atmosphere, PdCl2(dppf)·CH2Cl2 (245 mg, 300 mumol), potassium acetate (2.94 g, 30.0 mmol) and bis(pinacolato)diboron (2.79 g, 11.0 mmol) were sequentially added to a DMSO (30 mL) solution of Compound (13) (2.34 g, 10.0 mmol) at room temperature, and the mixture was stirred at 85 C for 18 hours. The mixture was cooled to room temperature, and then water (250 mL) was added to the mixture and the mixture was extracted with ethyl acetate (100 mL × 3). All the organic phases were mixed, sequentially rinsed with water (100 mL × 3) and a saline solution (100 mL × 1), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (60 g of silica gel, n-hexane/EtOAc = 5/1) to obtain Compound (14) as a colorless solid. TLC Rf = 0.41 (n-hexane/EtOAc = 2/1) 1H NMR (300 MHz, CDCl3) delta 1.35 (s,12H,4CH3), 4.72 (s, 2H, benzylic CH2), 7.34-7.41 (AA'BB', 2H, aromatic), 7.78-7.84 (AA'BB', 2H, aromatic).

Reference： [1]Patent: CN109694382,2019,A .Location in patent: Paragraph 0020-0023; 0028-0031
[2]Chemistry - A European Journal,2019,vol. 25,p. 3262 - 3266
[3]Patent: EP2450354,2012,A1 .Location in patent: Page/Page column 19-20

21
[ 18282-51-4 ]
[ 52222-73-8 ]
[ 1393125-26-2 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;copper(l) iodide; 4R-4-hydroxyproline; In dimethyl sulfoxide; at 85℃; for 20h;	Intermediate (1): (4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)methanol A mixture of (4-iodophenyl)methanol (1030 mg, 4.41 mmol), <strong>[52222-73-8]4-(trifluoromethyl)-1H-pyrazole</strong> (600 mg, 4.41 mmol), copper (I) iodide (168 mg, 0.882 mmol), trans-4-hydroxy-L-proline (231 mg, 1.76 mmol) and cesium carbonate (2900 mg, 8.82 mmol) in dimethylsulfoxide (7.5 mL) was heated to 85 C. for 20 hours. The mixture was diluted with water and extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-45% ethyl acetate in heptane), gave (4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)methanol. 1H NMR (400 MHz, CDCl3, delta): 8.16 (s, 1H), 7.89 (s, 1H), 7.65 (d, J=8.39 Hz, 2H), 7.47 (d, J=8.39 Hz, 2H), 4.74 (d, J=5.66 Hz, 2H), 1.85 (t, J=5.86 Hz, 1H).

Reference： [1]Patent: US2012/202834,2012,A1 .Location in patent: Page/Page column 15

22
[ 18282-51-4 ]
[ 355025-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 1.75 h / 20 °C 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.33 h / -78 °C 2.2: 16 h / -78 - 35 °C 3.1: phenyl isocyanate; triethylamine / toluene / 4 h / 20 - 80 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.58 h / 0 °C 5.1: tetrachloromethane; triphenylphosphine / dichloromethane / 0.33 h / 20 - 50 °C 6.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 19 h / 20 °C 7.1: diphenyl phosphoryl azide; triethylamine / toluene / 0.5 h / 120 °C 8.1: tetra-(n-butyl)ammonium iodide; triethylamine / dichloromethane / 2 h / 50 °C

Reference： [1]Sato, Takanao; Sugimoto, Kenji; Inoue, Asuka; Okudaira, Shinichi; Aoki, Junken; Tokuyama, Hidetoshi [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 13, p. 4323 - 4326]

23
[ 18282-51-4 ]
[ 1774-35-2 ]
[ 620-94-0 ]
[ 15164-44-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 99% 2: 88%	With per-rhenic acid In toluene for 17h; Reflux;	General procedure: In a typical experiment, to a solution of HReO4 (5.0 mol %) in toluene (3 mL) was added the 4-methylphenyl sulfoxide (1.0 mmol) and the alcohol (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Tables 1-3) and the progress of the reactions was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford the carbonyl compounds and 4-methylphenyl sulfide, which are all known compounds.

Reference： [1]Sousa, Sara C. A.; Bernardo, Joana R.; Fernandes, Ana C. [Tetrahedron Letters, 2012, vol. 53, # 46, p. 6205 - 6208,4]

24
[ 302348-51-2 ]
[ 18282-51-4 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 140 - 143

25
[ 593-39-5 ]
[ 18282-51-4 ]
C₂₅H₃₉IO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid In acetonitrile at 80℃; for 1h;

Reference： [1]Pham, Huong T.; Trevitt, Adam J.; Mitchell, Todd W.; Blanksby, Stephen J. [Rapid Communications in Mass Spectrometry, 2013, vol. 27, # 7, p. 805 - 815]

26
[ 936-49-2 ]
[ 18282-51-4 ]
[ 1427476-01-4 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 3470 - 3475

27
[ 18282-51-4 ]
[ 3058-39-7 ]

Yield	Reaction Conditions	Operation in experiment
99%		General procedure: With respect to 2 mmol of each alcohol represented by the general formula (1), 4 ml of CH 2 Cl 2 as a solvent, 0.05 equivalent of TEMPO as an N-nitrosyl compound, (A) t-BuOCl, (B) I 2 or (C ) N, N'-diiodo-5,5-dimethylhydantoin (DIH) were mixed in a predetermined amount and stirred for a predetermined time at room temperature.Next, 1.5 equivalents of I 2 and 4 ml of aqueous ammonia were added, and the mixture was stirred at room temperature for 2 hours.

Reference： [1]Synthesis,2013,vol. 45,p. 2155 - 2164
[2]Patent: JP2015/40203,2015,A .Location in patent: Paragraph 0041-0043; 0045
[3]Journal of the Iranian Chemical Society,2015,vol. 12,p. 107 - 111
[4]European Journal of Organic Chemistry,2019,vol. 2019,p. 3190 - 3194
[5]Green Chemistry,2019,vol. 21,p. 4334 - 4340

28
[ 67-56-1 ]
[ 18282-51-4 ]
[ 619-44-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate at 55℃; for 24h;	S6. Procedure for the synthesis of esters General procedure: A magnetic stir bar and the alcohol substrate were transferred to 20 mL glass tube and then 2 mL of MeOH oralcohol was added. Then, 35 mg catalyst and 10 mol% of K2CO3 were added. The glass tube containingreaction mixture was fitted with septum and connected to a balloon containing one bar air. Then the glass tubewas placed into a preheated aluminum block at 60°C. Temperature inside the reaction tube was measured tobe 55 oC and this temperature has been taken as the reaction temperature. After completion of the reaction,the glass tube was cooled down to room temperature. Af terwards, the catalyst was f iltered-off and washedwith methanol. The solvent from the filtrate containing the reaction products was removed in vacuum and thecorresponding ester was purified by column chromatography. Products were analyzed by GC-MS and NMRspectroscopy analysis. In the case of yields determined the by GC, 100 μL n-hexadecane was added to thereaction vial containing the products and diluted with ethyl acetate. Then catalyst was f iltered through a plugof silica and the filtrate containing product was analyzed by GC.
77%	With Oxone; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide at 60℃; for 48h; Sealed tube;
94 %Chromat.	With oxygen; potassium carbonate at 60℃; for 24h; Schlenk technique; Green chemistry;

> 99 %Chromat.	With carbon-nitrogen embedded cobalt nanoparticles ⁽⁸⁰⁰⁾; air In hexane at 25℃; for 96h;
35 %Chromat.	With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; (2-((2-(diphenylphosphanyl)ethyl)(quinolin-2-ylmethyl)amino)ethyl)diphenylphosphine oxide; potassium carbonate In n-heptane at 120℃; for 16h;

Reference： [1]Bartling, Stephan; Beller, Matthias; Chandrashekhar, Vishwas G.; Jagadeesh, Rajenahally V.; Rabeah, Jabor; Rockstroh, Nils; Senthamarai, Thirusangumurugan [Chem, 2022, vol. 8, # 2, p. 508 - 531]
[2]Ray, Ritwika; Jana, Rahul Dev; Bhadra, Mayukh; Maiti, Debabrata; Lahiri, Goutam Kumar [Chemistry - A European Journal, 2014, vol. 20, # 47, p. 15618 - 15624]
[3]Jagadeesh, Rajenahally V.; Junge, Henrik; Pohl, Marga-Martina; Radnik, Joerg; Brueckner, Angelika; Beller, Matthias [Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10776 - 10782]
[4]Zhong, Wei; Liu, Hongli; Bai, Cuihua; Liao, Shijun; Li, Yingwei [ACS Catalysis, 2015, vol. 5, # 3, p. 1850 - 1856]
[5]Jiang, Xiaolin; Zhang, Jiahui; Zhao, Dongmei; Li, Yuehui [Chemical Communications, 2019, vol. 55, # 19, p. 2797 - 2800]

29
[ 18282-51-4 ]
[ 78712-43-3 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 127 - 131
Angew. Chem.,2014,vol. 126,p. 5131 - 5135

30
[ 18282-51-4 ]
[ 87736-88-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C 2.2: 1.25 h / -78 °C 3.1: pyridine; hydroxylamine hydrochloride / ethanol / 60 °C 4.1: triethylamine; dmap / dichloromethane / 20 °C 5.1: ammonium hydroxide / tetrahydrofuran / 48 h / -78 - 20 °C / Sealed tube 6.1: triethylamine; iodine / methanol / 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

Reference： [1]Nakamoto, Kosuke; Ueno, Yoshihito [Journal of Organic Chemistry, 2014, vol. 79, # 6, p. 2463 - 2472]

31
[ 18282-51-4 ]
[ 3470-50-6 ]
[ 1487093-89-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate; In acetone; for 6h;Reflux;	General procedure: <strong>[3470-50-6]6-Hydroxy-1-tetralone</strong> (0.3 g, 1.85 mmol) was suspended in acetone (15 mL) containing K2CO3 (3.70 mmol). The reaction was treated with an appropriately substituted arylalkyl bromide (2.035 mmol) and heated under reflux for 6 h. The reaction progress was monitored using silica gel TLC with ethyl acetate:petroleum ether (1:2) as mobile phase. Upon completion, the reaction was filtered through a pad of celite and concentrated in vacuo. The crude thus obtained was purified by recrystallization from cyclohexane.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2758 - 2763

32
[ 119072-55-8 ]
[ 18282-51-4 ]
[ 874-89-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With copper (II) trifluoroacetate hydrate; palladium diacetate; In dimethyl sulfoxide; at 130℃; for 6h;Sealed tube; Inert atmosphere;	General procedure: Aryl iodide (0.7 mmol, 1 equiv), tert-butyl isocyanide (2.1 mmol, 237 muL, 3 equiv), Pd(OAc)2 (0.035 mmol, 8 mg, 5 mol %), Cu(TFA)2*xH2O (1.4 mmol, 405 mg, 2 equiv) and DMSO (2.5 mL) were added to a 15 mL sealed tube, and stirred at 130 C for 4-12 h under nitrogen. After completion of the reaction indicated by TLC, the mixture was extracted with Et2O (510 mL). The combined organic phases was dried over Na2SO4, and concentrated under vacuum. Then the residue was purified by column chromatography on silica gel using petroleum ether (30-60 C)/Et2O as eluant to provide the pure target product.

Reference： [1]Tetrahedron,2015,vol. 71,p. 4883 - 4887

33
[ 541-59-3 ]
[ 18282-51-4 ]
[ 1607804-21-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 13h;
64%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 13h;	1.1 (1) N-(4-iodobenzyl) maleimide DIAD (12 mmol, 2.43 g, 2.40 mL, 1.2 eq.) was added over the course of one hour to a solution of 4-iodobenzyl alcohol (10 mmol, 2.34 g, 1.0 eq.), PPh3 (11 mmol, 2.88 g, 1.1 eq.), and maleimide (11 mmol, 1.07 g, 1.1 eq.) in 100 mL of THF. After the resulting yellow solution was stirred 12 h at room temperature, the solvent was removed by rotary evaporation and the residue was purified by column chromatography on silica gel (hexanes:ethyl acetate = 1:5) and washed with hexane to obtain 2.00 g (64%) of N-(4-iodobenyl)maleimide as a colorless solid.1H NMR (CD3CN, 400 MHz): δ 7.68 (d, J = 8.4 Hz, 2 H), 7.06 (d, J = 8.4 Hz, 2 H), 6.79 (s, 2 H), 4.57 (s, 2 H); 1H NMR (C6D6, 400 MHz): d 7.35 (d, J =8.0 Hz, 2 H), 6.81 (d, J = 8.4 Hz, 2 H), 5.61 (s, 2 H), 4.13 (s, 2 H); 13C NMR (100 MHz, CD3CN) δ 169.1, 136.0, 135.2,132.8, 128.1, 90.7, 38.7; HRMS (EI) Calcd for C11H8NO2I (M)+ : 312.9600; Found: 312.9608.

Reference： [1]Qin, Linlin; Hu, Bao; Neumann, Kiel D.; Linstad, Ethan J.; McCauley, Katelyenn; Veness, Jordan; Kempinger, Jayson J.; DiMagno, Stephen G. [European Journal of Organic Chemistry, 2015, vol. 2015, # 27, p. 5919 - 5924]
[2]Current Patent Assignee: UNIVERSITY OF NEBRASKA SYSTEM - WO2016/201125, 2016, A1 Location in patent: Page/Page column 17-18

34
[ 18282-51-4 ]
[ 1066-54-2 ]
[ 275386-60-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20℃;	A suspension of (4-iodophenyl)methanol (3.00 g, 13.64 mmol), ethynyltrimethylsilane (2.13 mL, 15.38 mmol), copper (_) iodide (122 mg, 0.64 mmol), bis(triphenylphosphine)palladium(II) dichloride (450 mg, 0.64 mmol), TEA (5.36 ml, 38.46 mmol) were stirred in THF (22 mL) at ambient temperature for overnight. The reaction solvent was evaporated under reduced pressure, and the residue was purified by column chromatography with hexane/ethyl acetate (20/1, v/v) to obtain the compound 53 (2.66 g, quant. yield): 1H NMR (400 MHz, CDCl3) _ 7.44 (d, J = 8.4 Hz, 2H), 7.26 (d, J = 8.5 Hz, 2H), 4.63 (s, 2H), 2.17 (bs, 1H), 0.25 (s, 9H); 13C NMR (100 MHz, CDCl3) _ 141.3, 132.2, 126.7, 122.4, 105.0, 94.3, 64.9, 0.1.
78%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; at 20℃; for 12h;	To a solution of 4-iodobenzyl alcohol (400 mg, 1.7 mmol), Pd(PPh3)4 (98 mg, 0.08 mmol), and CuI (14 mg, 0.008 mmol) in triethylamine(15 mL) was added ethynyltrimethylsilane (500 mg, 0.005 mol) at rt. After the reaction mixture was stirred at rt for 12 h, saturatedaq. NH4Cl was added, and the mixture was extracted with EtOAc. The combined organic phases were washed with brine, dried andconcentrated. Flash column chromatography with hexanes/EtOAc (5/1) as the eluent gave 4 (270 mg, 78%).

Reference： [1]Patent: WO2018/160967,2018,A1 .Location in patent: Page/Page column 86
[2]Chemistry - A European Journal,2019,vol. 25,p. 16270 - 16276
[3]Letters in Organic Chemistry,2019,vol. 16,p. 2 - 5
[4]Journal of the American Chemical Society,2015,vol. 137,p. 14319 - 14328

35
[ 1001-75-8 ]
[ 18282-51-4 ]
4-iodobenzyl 4-methylpent-4-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 24℃; for 2h; Inert atmosphere;

Reference： [1]Ma, Xiaoshen; Dang, Hester; Rose, John A.; Rablen, Paul; Herzon, Seth B. [Journal of the American Chemical Society, 2017, vol. 139, # 16, p. 5998 - 6007]

36
[ 18282-51-4 ]
[ 108-95-2 ]
[ 2215-78-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium phosphate; copper(l) iodide; N-(2-phenylphenyl)-N′-benzyl oxalamide In acetonitrile at 90℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;

Reference： [1]Zhai, Yuntong; Chen, Xiaofei; Zhou, Wei; Fan, Mengyang; Lai, Yisheng; Ma, Dawei [Journal of Organic Chemistry, 2017, vol. 82, # 9, p. 4964 - 4969]

37
[ 18282-51-4 ]
[ 20277-69-4 ]
[ 22821-77-8 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 6589 - 6599
[2]Chinese Journal of Chemistry,2017,vol. 35,p. 1661 - 1664

38
[ 18282-51-4 ]
[ 51173-05-8 ]
5-fluoro-1-(4-(hydroxymethyl)phenyl)pyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 115℃; for 16h;Inert atmosphere;	To a mixture of (4-iodophenyl)methanol (250 mg, 1.07 mmol) and <strong>[51173-05-8]5-fluoropyridin-2-ol</strong>(121 mg, 1.07 mmol) in dioxane (2 inL) was added CS2C03 (696 mg, 2.14 mmol) and N,N-dimethylethylenediamine (141 mg, 1.60 mmol). The mixture was degassed with argon for20 mm. Copper (I) iodide (203 mg, 1.07 mmol) was added and the reaction mixture was heated to 115 C for 16 hrs. The reaction mixture was allowed to cool to RT, filtered and concentrated in vacuo. The residue was added to a silica gel (40 g) column and was eluted with 0-20% MeOH in DCM. Fractions containing Compound 37c were combined and thesolvent removed to yield an off white solid (46 mg, 0.21 mmol, 21 % yield). lB NMR (500MHz, CDCI3) 5 7.53 (d, J= 8,6 Hz, 2H), 7.41 (d, J 8.4 Hz, 2H), 7.37-7.40 (m, 1H), 7.31 (t, J= 4.0 Hz, IH), 6.66 (dd, J= 5.4, 9.5 Hz, 1H), 4.79 (s, 2H).

Reference： [1]Patent: WO2017/96130,2017,A1 .Location in patent: Page/Page column 89; 90

39
[ 175676-42-3 ]
[ 18282-51-4 ]
1-iodo-4-((trifluoromethoxy)methyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 70℃; for 26h; Inert atmosphere; Sealed tube;

Reference： [1]Jiang, Xiaohuan; Deng, Zhijie; Tang, Pingping [Angewandte Chemie - International Edition, 2018, vol. 57, # 1, p. 292 - 295][Angew. Chem., 2018, vol. 130, # 1, p. 298 - 301,4]

40
[ 18282-51-4 ]
[ 619-58-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen; In 1,2-dichloro-ethane; at 25℃; for 48h;Schlenk technique;	General procedure: To a Schlenk tube were added Fe(NO3)3·9H2O (40.6 mg, 0.1 mmol), TEMPO (15.8 mg, 0.1 mmol), KCl (7.5 mg, 0.1 mmol), 1a (108.5 mg, 1.0 mmol), and DCE (4.0 mL) sequentially under an atmosphere of oxygen (gas bag, commercial size: 2 L, which could be expanded to 5 L). The mixture was then stirred at 25 C until completion of the reaction as monitored by TLC (petroleum ether/EtOAc = 5:1) (48h). The crude reaction mixture was filtered through a short column of silica gel (height: 2 cm, diameter: 3 cm) eluting with Et2O (3 × 25 mL). After evaporation, the residue was purified by chromatography on silica gel [petroleum ether/EtOAc = 15:1 (500 mL) to 2:1 (300 mL)] to afford benzoic acid (2a)14 (69.9 mg, 57%) as a pale yellow solid. Yields of 57% of 2a and 38% of benzaldehyde (3a)15 were observed by NMR analysisof the crude product using CH2Br2 as an internal standard and by comparison with spectra reported in the literature.
93%	With diethylene glycol dimethyl ether; at 70℃; for 0.5h;Sonication;	In a 10 mL round bottom flask, 1.17 g of 4-iodobenzyl alcohol and 2 g of diethylene glycol dimethyl ether were sequentially added.The resulting mixture was subjected to ultrasonic irradiation at 40 kHz/30 W/70 C for 30 minutes in an ultrasonic reaction apparatus. Diethylene glycol dimethyl ether was removed under reduced pressure and recrystallized to give 1.15 g of 4-iodobenzoic acid, yield 93%.

Reference： [1]Synthesis,2018,vol. 50,p. 1629 - 1639
[2]Patent: CN108467342,2018,A .Location in patent: Paragraph 0148; 0149
[3]Green Chemistry,2018,vol. 20,p. 3038 - 3043
[4]ACS Catalysis,2018,vol. 8,p. 3754 - 3763

41
[ 18282-51-4 ]
[ 619-58-9 ]
[ 15164-44-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 86% 2: 14 %Spectr.	With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48h; Schlenk technique;	General procedure: To a Schlenk tube were added Fe(NO3)3·9H2O (40.6 mg, 0.1 mmol), TEMPO (15.8 mg, 0.1 mmol), KCl (7.5 mg, 0.1 mmol), 1a (108.5 mg, 1.0 mmol), and DCE (4.0 mL) sequentially under an atmosphere of oxygen (gas bag, commercial size: 2 L, which could be expanded to 5 L). The mixture was then stirred at 25 °C until completion of the reaction as monitored by TLC (petroleum ether/EtOAc = 5:1) (48h). The crude reaction mixture was filtered through a short column of silica gel (height: 2 cm, diameter: 3 cm) eluting with Et2O (3 × 25 mL). After evaporation, the residue was purified by chromatography on silica gel [petroleum ether/EtOAc = 15:1 (500 mL) to 2:1 (300 mL)] to afford benzoic acid (2a)14 (69.9 mg, 57%) as a pale yellow solid. Yields of 57% of 2a and 38% of benzaldehyde (3a)15 were observed by NMR analysisof the crude product using CH2Br2 as an internal standard and by comparison with spectra reported in the literature.
	With tert.-butylnitrite; oxygen In [D₃]acetonitrile at 80℃; for 7h; Sealed tube; Green chemistry;

Reference： [1]Jiang, Xingguo; Ma, Shengming [Synthesis, 2018, vol. 50, # 8, p. 1629 - 1639]
[2]Wang, Man; Liang, Gan; Wang, Yunhao; Fan, Tao; Yuan, Baoling; Liu, Mingxian; Yin, Ying; Li, Liangchun [Chemistry - A European Journal, 2021, vol. 27, # 37, p. 9674 - 9685]

42
[ 18282-51-4 ]
[ 1341039-29-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; <i>L</i>-proline; copper(l) iodide; sodium L-ascorbate; sodium azide / dimethyl sulfoxide; water / 80 °C / Inert atmosphere 2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 0.17 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: ORION OYJ; ORION S R L - WO2018/115591, 2018, A1

43
[ 18282-51-4 ]
[ 3956-07-8 ]
4-iodo-N-(4-iodobenzoyl)benzamidium hydroxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium hypochlorite; sodium iodide In methanol; water; acetonitrile at 80℃; for 8h; Inert atmosphere;	Benzamide derivatives were synthesized according to the developed earlier method [2] with minor modifications (Scheme 1). A mixture of NaI (2 mmol) and a substituted amide (1.5 mmol) was added to amixture of solvents (CH3OH/CH3CN 20 mL), and subsequently substituted benzyl alcohols (1 mmol) and NaOCl (8 mmol, 70 wt % in H2O) were added under the atmosphere of argon. The reaction mixture was stirred for ca 8 h at 80 °C. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was cooled to room temperature and poured into crushed ice. The corresponding precipitated product was filtered off and recrystallized from asuitable solvent(s). The colorless crystals of 2 wereobtained after re-crystallization from acetone.

Reference： [1]Raheel; Imtiaz-ud-Din; Taj; Tahir; Al-Shakban [Russian Journal of General Chemistry, 2018, vol. 88, # 7, p. 1508 - 1514]

44
[ 18282-51-4 ]
[ 4786-76-9 ]
C₁₄H₁₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; copper(l) iodide In diethylene glycol dimethyl ether at 120℃; Inert atmosphere;	R2b Step 1 General procedure: Preparation Rib (746 mg, 5 mmol, 1 eq.), hctcroary 1/aryl- iodide (10 mmol), Cul (286 mg, 1.5 mmol, 0.3 eq.), 7?,7?-diaminocyclohexane (171 mg, 1.5 mmol, 0.3 eq.), anhydrous K3P04 (4.24 g, 20 mmol, 4 eq.) was stirred in diglyme (15 ml) for 6-16 hours at 120 °C under N2 atmosphere. (0135) Work-up 1 : (0136) After the reaction completed, the mixture was diluted with water (200 ml) (or 25 % aq. NH3) and cooled to r.t. The mixture was filtered, washed with water (3 x 30 ml), aq. NH3 solution (40 ml, 25 %), water (3 x 50 ml), heptane (50 then 30 ml) and dried in vacuum. Work-up 2: (0137) The reaction mixture was evaporated to Celite and purified by flash chromatography (heptane : EEO, gradient).

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC; SERVIER MONDE - WO2019/105963, 2019, A1 Location in patent: Page/Page column 18; 19; 27

45
[ 18282-51-4 ]
[ 13629-22-6 ]
[ 1836-87-9 ]
[ 1572-46-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 25% 2: 40%	With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); 1,3-bis-(diphenylphosphino)propane; potassium <i>tert</i>-butylate In 1,4-dioxane at 110℃; for 9h; Inert atmosphere;	General procedure for Ni-catalyzed reaction of 9-fluorenone hydrazone and benzylic alcohols General procedure: An oven-dried 25-mL flask was charged with t-BuOK (0.75 mmol), Ni(PPh3)2(1-naphthyl)Cl (0.025 mmol) and DPPP (0.025 mmol). Then the 9-fluorenone hydrazone (0.5 mmol) and the benzyl alcohol (1.5 mmol) (if solid) were added. The flask was evacuated and backfilled with nitrogen, with the operation being repeated twice. Dried 1,4-dioxane (4 mL) and the benzyl alcohol (1.5 mmol) (if liquid) were added via syringe at this time. The reaction mixture was performed on WATTECS WP-TEC-1020 parallel reactor of 110 °C for 9 h and then allowed to cool to room temperature; it was then filtered through a silica-gel pad that was washed with ethyl acetate. The combined organic phases were evaporated under reduced pressure and the residue purified by silica-gel column chromatography to give the desired products.

Reference： [1]Fan, Jiang-Tao; Fan, Xin-Heng; Chen, Yong-Jie; Gao, Cai-Yan; Yang, Lian-Ming [Synthetic Communications, 2019, vol. 49, # 21, p. 2895 - 2902]

46
[ 18282-51-4 ]
[ 66003-78-9 ]
[ 91718-22-8 ]

Reference： [1]Chemistry - An Asian Journal,2019,vol. 14,p. 3370 - 3379

47
[ 18282-51-4 ]
[ 603-33-8 ]
[ 3597-91-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrabutylammomium bromide; potassium acetate; palladium diacetate; tris-(o-tolyl)phosphine; In 1-methyl-pyrrolidin-2-one; at 110℃; for 4h;Schlenk technique; Inert atmosphere;	General procedure: Cross-coupling of 1a with Bi(p-tolyl) 3 : An oven-dried Schlenk tube was charged with (2-iodophenyl)methanol (1a) (0.75 mmol, 3 equiv.), Bi(p-tolyl) 3 (0.25 mmol, 1 equiv.), Pd(OAc) 2 (0.025 mmol, 0.1 equiv.), P(o-tolyl) 3 (0.1 mmol, 0.4 equiv.), KOAc(1.5 mmol, 6 equiv.), TBAB (0.75 mmol, 3 equiv.) and NMP (3 mL) under a N 2atmosphere. The mixture was stirred in an oil bath at 110 C for 4 h. The contents were quenched with water (10 mL) at rt and extracted with ethylacetate (30 mL). The organic extract was washed with brine and dried usingMgSO 4 . The organic solvent was removed under reduced pressure to obtain thecrude product. It was puried by silica gel chromatography using hexane/ethylacetate as eluent. The product 2a was obtained in 74% yield. The spectralcharacterization data for all the products is given in the Supporting information.

Reference： [1]Tetrahedron Letters,2020

48
[ 1798-06-7 ]
[ 18282-51-4 ]
[ 15164-44-0 ]

Reference： [1]Journal of the American Chemical Society,2020

49
[ 18282-51-4 ]
[ 57-13-6 ]
[ 4949-44-4 ]
C₁₅H₁₇IN₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With copper(II)-manganese(II) bimetallic complex immobilized on magnetite nanoparticles; air In neat (no solvent) at 70℃; for 2h; Green chemistry;	General procedure: For the Biginelli reaction, benzyl alcohol (1.2mmol),ethyl acetoacetate (1.2mmol), and urea (1.0mmol) were reacted in the presence of Fe3O4Cu-Mn catalyst (0.008g,0.280mol% Cu, 0.078mol% Mn) under solvent-free and aerobic conditions at 70°C. Repeatedly, the reaction performance and product purification was as same as the benzimidazole reaction. After the reaction completion, the magnetic catalyst was separated easily by an external magnet and the product was extracted to dichloromethane (3 × 5mL).The organic layers were combined, dried over Na2SO4 and purified by silica-gel column chromatography (n-hexane:EtOAc = 12: 3). The products were characterized and identified by comparing their melting point and NMR analyses with those authentic samples.

Reference： [1]Nasseri, Mohammad Ali; Rezazadeh, Zinat; Kazemnejadi, Milad; Allahresani, Ali [Catalysis Letters, 2021, vol. 151, # 4, p. 1049 - 1067]

50
[ 21256-18-8 ]
[ 18282-51-4 ]
4-iodobenzyl 3-(4,5-diphenyloxazol-2-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With dmap; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 12h; Schlenk technique;
	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 10h;

Reference： [1]Du, Yiming; Chen, Shuxin; Huang, Ao; Chen, Yihan; Liu, Yun-Lin; Song, Gaopeng; Tang, Ri-Yuan; Xu, Hanhong; Yao, Guangkai; Li, Zhaodong [Organic Letters, 2022, vol. 24, # 6, p. 1341 - 1345]
[2]Guo, Wen-Ting; Zhu, Bo-Han; Chen, Yi; Yang, Jian; Qian, Peng-Cheng; Deng, Chao; Ye, Long-Wu; Li, Long [Journal of the American Chemical Society, 2022, vol. 144, # 15, p. 6981 - 6991]

51
[ 18282-51-4 ]
[ 3956-07-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With ammonium hydroxide In water at 120℃; for 24h; Sealed tube; Autoclave;	S8. Procedure for the synthesis of amides General procedure: A magnetic stir bar and the alcohol substrate were transferred to 8 mL glass vial and then 2 mL of H2O wasadded. Then, 3 mg catalyst was added followed by the addition of aq. NH3. Then, the vial was f itted with aseptum, cap, and needle. The reaction vials were placed into a 300 mL autoclave (8 vials containing differentsubstrates were placed at a time in the autoclave) and then the autoclave was pressurized with 10 bar air. Theautoclave was placed into an aluminium block and the temperature of the aluminum block was set in orderobtain 120 °C inside the autoclave. Temperature of the aluminum block was set to 130 oC to attain 120 oCinside the autoclave, which was considered as the reaction temperature. The reactions were allowed toprogress under continuous stirring for the required time at 120 °C. Af ter completion of the reaction, theautoclave was cooled down to room temperature and the remaining air was gradually discharged. Afterwards,the catalyst was f iltered-off and washed with methanol. The solvent f rom the f iltrate containing the reactionproducts was removed in vacuum and the corresponding amide was purified by column chromatography. Allproducts were analyzed by GC-MS and NMR spectroscopy analysis.

52
[ 10317-13-2 ]
[ 18282-51-4 ]
3-(4-(hydroxymethyl)phenyl)-2-phenylpropan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With nickel(II) chloride ethylene glycol dimethyl ether complex; trimethylsilyl bromide; C₅₃H₇₅CoN₅O₁₅⁽¹⁺⁾*ClO₄^(1-); ammonia hydrochloride; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc powder In acetonitrile at 20℃; for 16h; Inert atmosphere; Irradiation; regioselective reaction;

Reference： [1]Chaładaj, Wojciech; Gryko, Dorota; Ociepa, Michał; Potrząsaj, Aleksandra [Organic Letters, 2022, vol. 24, # 13, p. 2469 - 2473]

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[ CAS No. 18282-51-4 ] {[proInfo.proName]}

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[ 18282-51-4 ] Synthesis Path-Upstream 1~15

[ 18282-51-4 ] Synthesis Path-Downstream 1~52

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Aryls

Alcohols

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[ 18282-51-4 ]