Name: 4393-06-0|1-Phenylprop-2-en-1-ol|95% (stabilized with TBC)
Brand: Ambeed
SKU: A264132
Rating: 96 (35 reviews)

1
[ 4393-06-0 ]
[ 93-55-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With [Ru(η3:η3-C10H16)Cl2(benzimidazole)]; In glycerol; at 75℃; for 24h;Sealed tube; Inert atmosphere; Green chemistry;	General procedure: The corresponding allylic alcohol (1mmol) and the DES solvent (1g) were introduced into a sealed tube under a nitrogen atmosphere. Complex 1c (0.2-10mol%) was then introduced at room temperature, and the resulting solution was heated at 75C for the indicated time. The course of the reaction was monitored by regular sampling and analysis by GC. The validity of this method has been confirmed by analyzing mixtures of the corresponding allylic alcohol/carbonyl compound in known proportions under the same conditions. To evaluate the recyclability of complex 1c, the addition of successive amounts of 1-octen-3-ol to the reaction mixture at regular times was tested.
92%	With C13H21Cl2N3PRu(1+)*Cl(1-); potassium carbonate; In tetrahydrofuran; at 75℃; for 20h;Inert atmosphere; Sealed tube;Catalytic behavior;	General procedure: In a sealed tube, under nitrogen atmosphere, the ruthenium complex [RuCl2( 6-C6H6)(PTA-Me)] (3a) (0.02-0.1 mmol; 0.5-2.5 mol% of Ru) and K2CO3 (0.05-0.25 mmol; 1.25-6.25 mol%) were added to a solution of the corresponding allylic alcohol 4a-o (4 mmol) in tetrahydrofuran (4 mL), and the resulting mixture stirred at 75 C for the indicated time (see Table 4 and Scheme 3). The course of the reaction was monitored by taking regularly samples of ca. 10 L which after dilution with dichloromethane (3 mL) were analyzed by GC. After the reaction was finished, the mixture was cooled to room temperature leading to the partial precipitation of 3a. The solid was separated by filtration and the reaction product isolated by solvent removal and chromatographic workup of the residue on silica-gel using a mixture of EtOAc-hexane (1:10) as eluent. The identity of the resulting carbonyl compounds 5a-o was assessed by comparison of their retention times with those of commercially available pure samples (Sigma-Aldrich or Acros Organics), by their fragmentation in GC/MS, and/or NMR spectroscopy.
81%	With (4-Me)Triaz(NHPiPr2)2Mn(CO)2Br; Cs2CO3; In tert-Amyl alcohol; at 135℃; for 24h;Inert atmosphere; Glovebox; Schlenk technique;	To a Schlenk flask (25 mL) equipped with a stir bar, precatalyst 1 (1.5 mol %), Cs2CO3 (8 mol%), a-vinylbenzyl alcohol (0.5 mmol), and tert-amyl alcohol were added under nitrogen atmosphere in a glove box. After completion of reaction, the solventwas removed, and the residue was purified by silica gel (100-200 mesh) column chromatography using ethyl acetate/hexane mixture as eluent. Yield was calculated for pure isolated product.

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2
[ 4393-06-0 ]
[ 33143-44-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 18h;	To a solution of 1-phenylprop-2-en-1-ol (1.44 g, 10.7 mmol) in DCM (30 mL) was added mCPBA (3.61 g, 16.1 mmol) slowly at rt. The mixture was stirred at rt for 18 h. Saturated NaHCO3/water was added, and the organics were extracted with DCM and EtOAc. The organic layer was concentrated. The residue was purified via silica gel chromatography (24g, hexanes-60%EtOAc) to give oxiran-2-yl(phenyl)methanol (1.46 g, 9.72 mmol, 91 % yield). (2247) 1H NMR (499 MHz, CDCl3) δ 7.47 - 7.39 (m, 4H), 7.38 - 7.34 (m, 1H), 4.99 - 4.50 (m, 1H), 3.29 - 3.24 (m, 1H), 3.02 - 2.88 (m, 1H), 2.88 - 2.78 (m, 1H).
75%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0℃; for 3h;Inert atmosphere;	Epoxidation of the secondary allyl alcohol 2a (400 mg, 2.98 mmol) was performed following the standard procedure by using mCPBA (670 mg, 3.87 mmol) in DCM (15 mL) at 0C under N2. The reaction was quenched with saturated aqueous sodium thiosulfate solution (2 mL). It was extracted with DCM (3 × 10 mL) and the combined extract was washed with saturated sodium bicarbonate solution (10 mL) and brine (10 mL) and finally dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue obtained was purified by column chromatography over silica gel (30% ethyl acetate in light petroleum) to yield (oxiran-2-yl)phenyl methanol 3a (327 mg, 75%) as an inseparable mixture of two isomers in 1:1 ratio. 1H NMR (500 MHz, CDCl3): δ 2.77 (t, J = 4.5 Hz, 1H), 2.78-2.87 (m, 1H), 2.98 (dd, J = 2.8, 4.8 Hz, 1/2H), 3.22-3.25 (m, 1H), 4.47 (d, J = 5.6 Hz, 1/2H), 4.94 (d, J = 3.2 Hz, 1/2H), 7.31-7.44 (m, 5H).

Reference： [1]Patent: WO2019/147782,2019,A1 .Location in patent: Page/Page column 742
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[12]Journal of Chemical Sciences,2016,vol. 128,p. 1067 - 1079
[13]European Journal of Organic Chemistry,2017,vol. 2017,p. 1502 - 1509

3
[ 4393-06-0 ]
[ 615-43-0 ]
[ 612-96-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With palladium diacetate; tetra-(n-butyl)ammonium iodide; triethylamine; In water; at 120℃; for 36h;	General procedure: To an oven-dried Schlenk tube charged with a magnetic stir bar wereadded o-iodoaniline 1 (1 equiv), allylic alcohol 2 (1.2 equiv), Pd(OAc)2(2 mol%), triethylamine (4 equiv), TBAI (2 equiv) and H2O (2 mL). Theresulting mixture was allowed to stir at 120 C (oil bath) for 36 h. Theprogress of the reaction was monitored by TLC (ethyl acetate/hexane,5:95 to 15:85). The reaction mixture was then cooled to room temperature,quenched with aqueous ammonium chloride solution andextracted with ethyl acetate (3 × 15 mL). The combined organic layerswere washed with saturated NaCl solution, dried (Na2SO4) and evaporatedunder reduced pressure. Purification of the crude material bysilica gel column chromatography (petroleum ether/ethyl acetate)furnished the quinolines 3.

Reference： [1]Synthesis,2022,vol. 54,p. 393 - 402
[2]Tetrahedron Letters,1991,vol. 32,p. 569 - 572

4
[ 4393-06-0 ]
[ 93-54-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With C35H41ClFeIrPS; hydrogen; sodium methylate; In tetrahydrofuran; at 25℃; under 22502.3 Torr; for 2h;Autoclave; Inert atmosphere;	General procedure: A solution containing 6.4 × 10-3mmol of precatalyst and0.13 mmol of substrate (20 equiv.) in 2 mL of THF was transferred into a 5 mL glass vial which was then placed under argon into a stainless steel autoclave equipped with a magnetic stirring bar. The reaction vessel was pressurized with H2 to 30 bar and stirred for the desired time at room temperature. Then pressure was released andthe reaction vessel was stirred for the desired time at controlledtemperature under a dihydrogen atmosphere at 1 bar. Alterna-tively, after venting the H2pressure used for the catalyst activation,the residual H2was purged with argon by continuous flushingbefore continuing the reaction. The pure products were obtainedby chromatography of the reaction mixture on silica gel using dichloromethane as eluent and then analyzed by NMR spectrosopyand chiral GC for the determination of the yields and enantiomeric excesses.
78%	With palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In dichloromethane; at 25℃; for 12h;Schlenk technique; Inert atmosphere;	Replace the gas environment in the Shrek tube with a nitrogen environment, add 3-phenylpropen-3-ol 0.25 mmol, palladium acetate 0.00125 mmol, methylene chloride 0.5 mL, add pinacol borane 0.275 mmol with stirring, room temperature conditions The reaction was carried out for 12 hours. The reaction solution obtained after the reaction was completed was subjected to column chromatography, and the target product obtained in 78% yield was a colorless liquid.

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[12]Inorganic Chemistry,2017,vol. 56,p. 11282 - 11298
[13]Zeitschrift fur Anorganische und Allgemeine Chemie,2021,vol. 647,p. 2157 - 2161

5
[ 4393-06-0 ]
[ 768-03-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 20℃; for 2h;Molecular sieve;	To a solution of 1a (0.670 g, 5 mmol, 1 eq.) in DCM (20 mL) were added 4-Å molecular sieves and N-methylmorpholine N-oxide (1.757 g, 15 mmol, 3 eq.). After stirring the solution for 5 minutes at room temperature, tetrapropylammonium perruthenate (0.105 g, 0.3 mmol, 0.06 eq.) was added. The reaction was stirred for 2 h, then it was filtered through Celite and washed with diethyl ether (20 ml). After concentration under vacuum, the crude product was purified by column chromatography (10 g silica gel, hexane - ethyl acetate, 8:2) to afford 1b (0.561g, 85 %) as a colourless oil, TLC petroleum ether -ethyl acetate, 1:1, Rf = 0.25
55%	With tert.-butylhydroperoxide;chromium(VI) oxide; In dichloromethane; water; at 0 - 20℃;	To a solution of phenyl allylic alcohol (3.0 g, 22.4 mmol) in CH2C12 was added Cr03 (112 mg, 1.12 mmol, 5 mol%). tBuOOH (70%, 7.2 M in H20, 10 mL, mmol, 3.2 eq. ) was added via a syringe at 0 C over 1h. The resulting brown mixture was stirred at room temperature overnight. The corresponding yellow suspension was added solid Na2S203 (20 g) at 0 C. The mixture was vigorously stirred at room temperature for 30 min. The resultant brown mixture was concentrated and extracted with ether (30 mL x 3). The combined extracts were washed with water, brine and over Na2S04 and concentrated. The residue was subjected to purification on silica gel (hexanes/EtOAc 20/1) to give a vinyl ketone (1.6 g, 55% yield) as a light yellow oil. (at)H NMR (CDCl3, 400 MHz) : No. ppm 7.93 (dd, J= 8.0,1.0 Hz, 2H), 7.42-7.46 (m, 3H), 7.14 (dd, J = 17.2, 10.4 Hz, IH), 6.43 (dd, J= 17.2, 1.0 Hz, IH), 5.92 (dd, J= 10.4, 1.0 Hz, IH).
	With manganese(IV) oxide; In dichloromethane; at 20℃;	To a stirred solution of acrylaldehyde (50 mmol) in THF (70 mL) under an N2 atmosphere, Grignard reagent (2.5 equiv., 125 mmol) was added via cannula, which had been freshly prepared in THF, at such a rate as to maintain the temperature below 0C. The resulting dark green suspension was allowed to slowly warm to room temperature over 2 hours. The mixture was quenched with saturated aqueous NH4Cl. The two phase mixture was separated by a separatory funnel. The aqueous layer was extracted by ether (3x50 mL) and the combined organic layers were washed with saturated aqueous NaHCO3 and saturated aqueous NaCl (100 mL), and dried over Na2SO4. It was purified by column chromatography to give alcohol. To the solution of alcohol in dichlormethane, MnO2 (7 equive) was added at room temperature. Then the black solide was separated by vacuum filter, and the filtrate was concentrated in vacuo. The crude product was futher purified by column chromatography. [Reference: Patrick P. Jean S. Applied Catalysis A: 2008, 336, 101-108.]

85%Chromat.	With sodium hypochlorite; (Et4N)2[FeIII(Cl)(biuret-TAML)]; In aq. phosphate buffer; acetonitrile; at 20℃; for 5h;pH 7.0;Catalytic behavior;	General procedure: To a reaction vial containing a magnetic stir bar, unsubstituted Fe-bTAML catalyst, 1 (0.2-0.8mM, 0.5-2mol %), substrate (40mM, 0.04mmol, 1.0equiv.) and pH 7 phosphate buffer (100mM, 300μL aqueous solution) in 700μL acetonitrile were added. An aqueous solution of sodium hypochlorite (2equiv.) was added via syringe pump with continuous stirring over a period of 2-6h at room temperature. The reaction was monitored by TLC and GC. After completion of the reaction, the solvent (CH3CN) was removed under reduced pressure. Saturated aqueous solution of sodium bicarbonate was added to the residual portion and extracted with dichloromethane (2times). The organic part was dried with anhydrous sodium sulphate, analysed by GC-MS to estimate the product GC yield.
	With [1-methyl-3-butylimidazolium][AuCl4] encapsulated in zeolitic imidazolate framework - 8-6.25%-900; In toluene; at 130℃; for 36h;Schlenk technique;	General procedure: In a typical run, alcohol (0.05 mmol), toluene (1 mL), and [Bmim][AuCl4] (at) ZIF-8-x-T (10 mol Au% based on alcohols) were added to a 25 mL Schlenk tube. The reaction mixture was stirred at 130 C under atmospheric air. After reaction, qualitative analyses of the reaction mixtures were performed on a GC-MS spectrometer (Agilent, 7890BGC/5977 A MS) equipped with a HP-5 MS capillary column (0.25mm×30 m).
	With pyridinium chlorochromate; In dichloromethane; for 3h;	Compound 1′R-C: add diatomite (3 g) into anhydrous dichloromethane (30 ml) solution of compound B (10.0 mmol) and stir for 5 min. Then add PCC (pyridinium chlorochromate onium salt, 2.56 g) and stir for 3 h. After vacuum concentration, the extract is isolated by fast silica gel column chromatography (n-hexane/ethyl acetate, 10:1), and generated ketone is obtained. Then, the generated ketone is dissolved in 5 ml THF solution and added into toluene solution of (R)-methyl-CBS oxazaborolidine catalyst (1.0 mol/L, 1 mmol, 1 mL) and methyl sulfide solution containing borane (10 mol/L, 1 mmol, 1 mL) at room temperature. Reaction mixture is stirred for 5 h at room temperature. After being added saturated ammonium chloride (10 ml), the mixture is extracted with aether (3×20 mL) and washed by saturated salt solution (2×10 mL), then dried by MgSO4 and evaporate to remove the solvent. The crude product is isolated by fast silica gel column chromatography (n-hexane/ethyl acetate, 10:1) and compound 1′R-C is obtained.

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6
[ 4393-06-0 ]
[ 103-49-1 ]
(E)-N,N-dibenzyl-3-phenylprop-2-en-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With dichloro[9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene]palladium(II); In isopropyl alcohol; at 20℃; for 12h;Inert atmosphere;	General procedure: General procedure for amination of allylic alcoholsAllylic alcohols 1 (0.4 mmol), Pd(Xantphos)Cl2 (0.02 mmol, 5 mol%), amines 2(0.6 mmol) and 2-PrOH (1.5 mL) were added to a 25 mL flame-dried Young-typetube under nitrogen atmosphere. The mixture was stirred at room temperature for 12hrs. After concentrated under reduced pressure, the residue was purified by flashcolumn chromatography on silica gel and eluted with EtOAc/PE (1/100-1/1) to affordthe desired product 3.

Reference： [1]Synlett,2014,vol. 25,p. 2781 - 2786
[2]Chemistry Letters,1995,p. 1121 - 1122
[3]Organic Letters,2017,vol. 19,p. 6148 - 6151

7
[ 610-99-1 ]
[ 4393-06-0 ]
[ 4439-45-6 ]
1,4-diphenyl-1,5-hexadiene [ No CAS ]
(E)-1-(2-Hydroxy-phenyl)-2-methyl-5-phenyl-pent-4-en-1-one [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 3113 - 3116

8
[ 2768-02-7 ]
[ 100-52-7 ]
[ 4393-06-0 ]

Yield	Reaction Conditions	Operation in experiment
100%		Example 6 Synthesis of an Alcohol To a DMF (0.2 mL) solution of CuF.3PPh3.2EtOH (10 mg, 0.01 mmol) as synthesized according to the method described in the foregoing publication and dppf (8 mg, 0.014 mmol) (this catalyst preparation method is designated as “A”; hereinafter the same), benzaldehyde (0.020 mL, 0.20 mmol) and vinyltrimethoxysilane (62 μL, 0.40 mmol) were added at room temperature under an argon atmosphere, the temperature was then raised to 60 C., and the mixture was stirred for 3 hours. Thereafter, the reaction mixture was allowed to stand for cooling to room temperature, to which was then added tetrabutylammonium fluoride (TBAF) (1M/THF, 0.5 mL), and the mixture was stirred for 10 minutes. After adding water, the mixture was extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After drying, the solvent was distilled off, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane: 1/9 to ¼), thereby obtaining desired 1-phenyl-2-propen-1-ol in a yield of 100%.
100%		Example 1 Synthesis of an Allylic Alcohol To a THF (0.3 mL) solution of CuF.3PPh3.2EtOH (20 mg, 0.02 mmol) as synthesized according to the method described in the publication Inorg. Chim. Acta, 1981, 52, 153, and 1,2-bis(diphenylphosphino)ethane (hereinafter abbreviated as “dppe”) (12 mg, 0.03 mmol), benzaldehyde (0.020 mL., 0.20 mmol) and vinyltrimethoxysilane (62 μL, 0.40 mmol) were added at room temperature under an argon atmosphere, the temperature was then raised to 60 C., and the mixture was stirred for 3 hours. Thereafter, the reaction mixture was allowed to stand for cooling to room temperature, to which was then added tetrabutylammonium fluoride (TBAF) (1M/THF, 0.5 mL), and the mixture was stirred for 10 minutes. After adding water, the mixture was extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After drying, the solvent was distilled off, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane: 1/9 to ¼), thereby obtaining desired 1-phenyl-2-propen-1-ol in a yield of 61%. Examples 2 to 5 The results obtained by carrying out the same operations as in Example 1, except for changing the ligand, are shown in Table 1. The abbreviations have the following meanings. d(p-Cl)ppe: 1,2-Bis(di-p-chlorophenylphosphino)ethane d(p-MeO)ppe: 1,2-Bis(di-p-methoxyphenylphosphino)ethane dppp: 1,3-Bis(diphenylphosphino)propane dppf: 1,1'-Bis(diphenylphosphino)ferrocene TABLE 1 Example Ligand Time (h) Yield (%) 2 d(p-Cl)ppe 24 47 3 d(p-MeO)ppe 24 57 4 dppp 24 89 5 dppf 4 100
89%		Example 1 Synthesis of an Allylic Alcohol To a THF (0.3 mL) solution of CuF.3PPh3.2EtOH (20 mg, 0.02 mmol) as synthesized according to the method described in the publication Inorg. Chim. Acta, 1981, 52, 153, and 1,2-bis(diphenylphosphino)ethane (hereinafter abbreviated as “dppe”) (12 mg, 0.03 mmol), benzaldehyde (0.020 mL., 0.20 mmol) and vinyltrimethoxysilane (62 μL, 0.40 mmol) were added at room temperature under an argon atmosphere, the temperature was then raised to 60 C., and the mixture was stirred for 3 hours. Thereafter, the reaction mixture was allowed to stand for cooling to room temperature, to which was then added tetrabutylammonium fluoride (TBAF) (1M/THF, 0.5 mL), and the mixture was stirred for 10 minutes. After adding water, the mixture was extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After drying, the solvent was distilled off, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane: 1/9 to ¼), thereby obtaining desired 1-phenyl-2-propen-1-ol in a yield of 61%. Examples 2 to 5 The results obtained by carrying out the same operations as in Example 1, except for changing the ligand, are shown in Table 1. The abbreviations have the following meanings. d(p-Cl)ppe: 1,2-Bis(di-p-chlorophenylphosphino)ethane d(p-MeO)ppe: 1,2-Bis(di-p-methoxyphenylphosphino)ethane dppp: 1,3-Bis(diphenylphosphino)propane dppf: 1,1'-Bis(diphenylphosphino)ferrocene TABLE 1 Example Ligand Time (h) Yield (%) 2 d(p-Cl)ppe 24 47 3 d(p-MeO)ppe 24 57 4 dppp 24 89 5 dppf 4 100

61%		Example 1 Synthesis of an Allylic Alcohol To a THF (0.3 mL) solution of CuF.3PPh3.2EtOH (20 mg, 0.02 mmol) as synthesized according to the method described in the publication Inorg. Chim. Acta, 1981, 52, 153, and 1,2-bis(diphenylphosphino)ethane (hereinafter abbreviated as “dppe”) (12 mg, 0.03 mmol), benzaldehyde (0.020 mL., 0.20 mmol) and vinyltrimethoxysilane (62 μL, 0.40 mmol) were added at room temperature under an argon atmosphere, the temperature was then raised to 60 C., and the mixture was stirred for 3 hours. Thereafter, the reaction mixture was allowed to stand for cooling to room temperature, to which was then added tetrabutylammonium fluoride (TBAF) (1M/THF, 0.5 mL), and the mixture was stirred for 10 minutes. After adding water, the mixture was extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After drying, the solvent was distilled off, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane: 1/9 to ¼), thereby obtaining desired 1-phenyl-2-propen-1-ol in a yield of 61%.
57%		Example 1 Synthesis of an Allylic Alcohol To a THF (0.3 mL) solution of CuF.3PPh3.2EtOH (20 mg, 0.02 mmol) as synthesized according to the method described in the publication Inorg. Chim. Acta, 1981, 52, 153, and 1,2-bis(diphenylphosphino)ethane (hereinafter abbreviated as “dppe”) (12 mg, 0.03 mmol), benzaldehyde (0.020 mL., 0.20 mmol) and vinyltrimethoxysilane (62 μL, 0.40 mmol) were added at room temperature under an argon atmosphere, the temperature was then raised to 60 C., and the mixture was stirred for 3 hours. Thereafter, the reaction mixture was allowed to stand for cooling to room temperature, to which was then added tetrabutylammonium fluoride (TBAF) (1M/THF, 0.5 mL), and the mixture was stirred for 10 minutes. After adding water, the mixture was extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After drying, the solvent was distilled off, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane: 1/9 to ¼), thereby obtaining desired 1-phenyl-2-propen-1-ol in a yield of 61%. Examples 2 to 5 The results obtained by carrying out the same operations as in Example 1, except for changing the ligand, are shown in Table 1. The abbreviations have the following meanings. d(p-Cl)ppe: 1,2-Bis(di-p-chlorophenylphosphino)ethane d(p-MeO)ppe: 1,2-Bis(di-p-methoxyphenylphosphino)ethane dppp: 1,3-Bis(diphenylphosphino)propane dppf: 1,1'-Bis(diphenylphosphino)ferrocene TABLE 1 Example Ligand Time (h) Yield (%) 2 d(p-Cl)ppe 24 47 3 d(p-MeO)ppe 24 57 4 dppp 24 89 5 dppf 4 100
47%		Example 1 Synthesis of an Allylic Alcohol To a THF (0.3 mL) solution of CuF.3PPh3.2EtOH (20 mg, 0.02 mmol) as synthesized according to the method described in the publication Inorg. Chim. Acta, 1981, 52, 153, and 1,2-bis(diphenylphosphino)ethane (hereinafter abbreviated as “dppe”) (12 mg, 0.03 mmol), benzaldehyde (0.020 mL., 0.20 mmol) and vinyltrimethoxysilane (62 μL, 0.40 mmol) were added at room temperature under an argon atmosphere, the temperature was then raised to 60 C., and the mixture was stirred for 3 hours. Thereafter, the reaction mixture was allowed to stand for cooling to room temperature, to which was then added tetrabutylammonium fluoride (TBAF) (1M/THF, 0.5 mL), and the mixture was stirred for 10 minutes. After adding water, the mixture was extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After drying, the solvent was distilled off, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane: 1/9 to ¼), thereby obtaining desired 1-phenyl-2-propen-1-ol in a yield of 61%. Examples 2 to 5 The results obtained by carrying out the same operations as in Example 1, except for changing the ligand, are shown in Table 1. The abbreviations have the following meanings. d(p-Cl)ppe: 1,2-Bis(di-p-chlorophenylphosphino)ethane d(p-MeO)ppe: 1,2-Bis(di-p-methoxyphenylphosphino)ethane dppp: 1,3-Bis(diphenylphosphino)propane dppf: 1,1'-Bis(diphenylphosphino)ferrocene TABLE 1 Example Ligand Time (h) Yield (%) 2 d(p-Cl)ppe 24 47 3 d(p-MeO)ppe 24 57 4 dppp 24 89 5 dppf 4 100

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 4138 - 4139
[2]Patent: US2006/199973,2006,A1 .Location in patent: Page/Page column 8
[3]Patent: US2006/199973,2006,A1 .Location in patent: Page/Page column 8
[4]Patent: US2006/199973,2006,A1 .Location in patent: Page/Page column 8
[5]Patent: US2006/199973,2006,A1 .Location in patent: Page/Page column 8
[6]Patent: US2006/199973,2006,A1 .Location in patent: Page/Page column 8
[7]Patent: US2006/199973,2006,A1 .Location in patent: Page/Page column 8

9
[ 4393-06-0 ]
[ 79-22-1 ]
[ 160879-62-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at -10 - 20℃; for 24h;	General procedure: To p-X-PhCH(CH=CH2)OH containing 5-10% p-X-PhCH2OH1 (20.0 mmol) and pyridine (30.0 mmol) in 20 mL CH2Cl2 at ca. -10 was added methyl chloroformate (22.0 mmol) dropwise over 30-40 min. The mixture was allowed to warm slowly to room temperature. After ca. 24 h, the reaction mixture was transferred to a separatory funnel containing 50 mL ether and 20 mL sat NaCl. The aqueous layer was separated and washed with 25 mL ether. The ether layers were combined and dried over CaCl2. The bulk of the ether was removed under reduced pressure in a rotary evaporator leaving a liquid that was chromatographed on silica gel and eluted with 4-5% ethyl acetate in hexanes (3a-d) or with 45:55 CH2Cl2-hexanes (3e). The desired carbonate was eluted first closely followed by the carbonate of the corresponding benzyl alcohol. Overall yields of p-X-PhCH(CH=CH2)OCO2CH3 from p-X-PhCHO were in the range of 28-35%.

Reference： [1]Advanced Synthesis and Catalysis,2020,vol. 362,p. 331 - 336
[2]Chemical Communications,2020,vol. 56,p. 454 - 457
[3]Angewandte Chemie - International Edition,2016,vol. 55,p. 13189 - 13194
Angew. Chem.,2016,vol. 128,p. 13383 - 13388,6
[4]Journal of the American Chemical Society,2006,vol. 128,p. 11770 - 11771
[5]Journal of Organic Chemistry,2007,vol. 72,p. 9018 - 9031
[6]Chemical Communications,2012,vol. 48,p. 6723 - 6725
[7]Tetrahedron Letters,2013,vol. 54,p. 5795 - 5798
[8]Organic Letters,2017,vol. 19,p. 5212 - 5215
[9]Chemistry - A European Journal,2017,vol. 23,p. 18156 - 18160

10
[ 75-77-4 ]
[ 4393-06-0 ]
[ 19917-00-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine; In dichloromethane; at 20℃; for 15h;	To a mixture of 1-phenylprop-2-en-1-ol (1.7 g, 12.7 mmol) and triethylamine (3.6 mL, 38.1 mmol, 3.0 equiv.) was added chlorotrimethylsilane (2.4 mL, 19.1 mmol, 1.5 equiv.), and resulting mixture was stirred for 15 hours at room temperature. The reaction was quenched with water, and the resulting mixture was extracted with hexane. The combined organic layers were washed with ice-cold 5% aqueous HCl solution and saturated aqueous NaHCO3 solution, dried over anhydrous MgSO4, filtered, and evaporated. Distillation (0.5 Torr) gave titled compound as colorless oil (2.0 g, 75%). The NMR data are in agreement with those previously reported in the literature.8 1H NMR (500 MHz, CDCl3): = 7.35-7.31 (m, 4 H), 7.26-7.23 (m, 1 H), 5.96 (ddd, J = 17.0, 9.5, 6.5 Hz, 1 H), 5.27 (d, J = 17.0 Hz, 1 H), 5.16 (d, J = 6.5 Hz, 1 H), 5.10 (d, J = 9.5 Hz, 1 H), 0.11 (s, 9 H). 13C NMR (125 MHz, CDCl3): = 143.3, 141.3, 128.2, 128.0, 127.1, 126.1, 114.0, 75.7, 0.2.

Reference： [1]European Journal of Organic Chemistry,2006,p. 4393 - 4397
[2]Synlett,2018,vol. 29,p. 1211 - 1214

11
[ 4393-06-0 ]
[ 100-61-8 ]
[ 33603-47-3 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 1982 - 1984
[2]Organic Letters,2010,vol. 12,p. 2726 - 2729
[3]Chemical Communications,2003,p. 234 - 235

12
[ 4393-06-0 ]
[ 4393-21-9 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 3139 - 3143

13
[ 4393-06-0 ]
[ 93-54-9 ]
[ 93-55-0 ]

Yield	Reaction Conditions	Operation in experiment
7%; 93%	With C35H41FePRhS; hydrogen; sodium methylate; In tetrahydrofuran; at 82℃; under 22502.3 Torr; for 16h;Autoclave; Inert atmosphere;	General procedure: A solution containing 6.4 × 10-3mmol of precatalyst and0.13 mmol of substrate (20 equiv.) in 2 mL of THF was transferred into a 5 mL glass vial which was then placed under argon into a stainless steel autoclave equipped with a magnetic stirring bar. The reaction vessel was pressurized with H2 to 30 bar and stirred for the desired time at room temperature. Then pressure was released andthe reaction vessel was stirred for the desired time at controlledtemperature under a dihydrogen atmosphere at 1 bar. Alterna-tively, after venting the H2pressure used for the catalyst activation,the residual H2was purged with argon by continuous flushingbefore continuing the reaction. The pure products were obtainedby chromatography of the reaction mixture on silica gel using dichloromethane as eluent and then analyzed by NMR spectrosopyand chiral GC for the determination of the yields and enantiomeric excesses.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2017,vol. 426,p. 376 - 380
[2]Journal of Organometallic Chemistry,2007,vol. 692,p. 4805 - 4808
[3]Green Chemistry,2009,vol. 11,p. 1992 - 2000

14
[ 4393-06-0 ]
[ 249647-24-3 ]
[ 1092491-66-1 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 8108 - 8111

15
[ 4393-06-0 ]
[ 14489-75-9 ]
[ 65472-88-0 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 2377 - 2379

16
[ 694-32-6 ]
[ 4393-06-0 ]
[ 1215309-36-6 ]
[ 1215309-23-1 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 1184 - 1187

17
[ 120-72-9 ]
[ 4393-06-0 ]
3-(1-phenylprop-2-en-1-yl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sulfuric acid; In water; acetonitrile; at 50℃; for 5h;Inert atmosphere; Schlenk technique;	General procedure: A N2 purged flame-dried Schlenk tube containing indole 1(0.200 mmol), [Ir(COD)Cl]2 (0.004mmol), were added successively CH3CN (1 mL), allylic alcohol 2(0.200 mmol) and H2SO4(1 M inH2O)(0.010 mmol) via syringe. The reaction mixture was stirred at 50 C for 5 h. After thereaction was complete, the solvent was removed under reduced pressure. The ratio ofregioisomers(branched/linear) was determined by 1H NMR of the crude reaction mixture. Thecrude residue was purified by flash column silica gel chromatography (petroleum ether/ ethylacetate: 95:5 to 90:10) to yield the product 3.

Reference： [1]Synthesis,2014,vol. 46,p. 1717 - 1724
[2]Angewandte Chemie - International Edition,2010,vol. 49,p. 2782 - 2785
[3]Angewandte Chemie - International Edition,2020,vol. 59,p. 7598 - 7604
Angew. Chem.,2020,vol. 132,p. 7668 - 7674,7

18
[ 4393-06-0 ]
[ 115314-14-2 ]
[ 1236375-68-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3809 - 3813

19
[ 51738-07-9 ]
[ 4393-06-0 ]
[ 1251839-60-7 ]

Reference： [1]Journal of Chemical Research,2010,p. 254 - 258

20
[ 4393-06-0 ]
[ 545-06-2 ]
[ 138313-59-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In hexane; at 0℃; for 0.75h;	To a suspension of 1-phenylallylalcohol (3f) (129 mg, 961 μmol) and Cl3CCN (555 mg, 3.85 mmol) in hexane (4 mL)was added DBU (35.9 mg, 236 μmol) at 0 C. After the suspension changed to be the solution (actual time = 45 min),hexane (5 mL) and saturated aq NH4Cl (10 mL) were added to the reaction mixture. The separated hexane layer was washedwith saturated aq NH4Cl (10 mL). The general drying procedure gave 4f (233 mg, 836 μmol, 87%) as a colorless oil. The1H NMR spectra were in good agreement with the literature data of 4f.9

Reference： [1]Synlett,2019,vol. 30,p. 1308 - 1312
[2]Organic Letters,2010,vol. 12,p. 4580 - 4583
[3]Chemical Communications,2012,vol. 48,p. 11531 - 11533,3

21
[ 93-89-0 ]
[ 1826-67-1 ]
[ 4393-06-0 ]

Yield	Reaction Conditions	Operation in experiment
65%		General procedure: To a solution of ethyl benzoate (0.14 g, 1.0 mmol) in THF (10 mL) was slowly added LDBBA (2.4 mL, 0.5 M in THF-hexane, 1.2 mmol) and the mixture was stirring for 3 h at 0 C. To this was slowly added n-butylmagnesium chloride (0.94 mL, 1.6 M in Et2O, 1.5 mmol). After being stirred for 30 min at room temperature, the reaction mixture was quenched with aqueous 1 N HCl (10 mL) and extracted with diethyl ether (2 × 10 mL). The combined organic layers were dried over MgSO4 and filtered. After the removal of solvents in vacuo, purification of the residue by column chromatography on silica gel gave 1-phenylpentan-1-ol (108 mg, 66%). All products in this Letter were confirmed by comparison with data reported in the literatures.5

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1718 - 1720

22
[ 4393-06-0 ]
[ 98-80-6 ]
[ 1083-30-3 ]

Yield	Reaction Conditions	Operation in experiment
53%	With [2,2]bipyridinyl; palladium diacetate; copper(l) chloride; In dimethyl sulfoxide; at 80℃; for 12h;Green chemistry;	General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 2.0 mmol heteroaryl boronic acids, 5 mol% CuCl, 10 mol% Pd(OAc)2, 1.0 mmol allyl alcohols, 30 mol% ligand (L4) and DMSO (3.0 mL). The mixture was stirred at 80 C for 12 h under air. After cooled to room temperature, the reaction mixture was diluted with 30 mL dichloromethane, and then washed with saturated NaCl aq (2 x 15 mL) and dried over Na2SO4. After that, the solvent was removed under reduced pressure and the product was purified by flash column chromatography. The products were characterized by 1H NMR, 13C NMR, HRMS and GC-MS.

Reference： [1]Green Chemistry,2014,vol. 16,p. 2788 - 2797
[2]European Journal of Organic Chemistry,2012,p. 4694 - 4698
[3]Advanced Synthesis and Catalysis,2012,vol. 354,p. 341 - 346
[4]Tetrahedron Letters,2018,vol. 59,p. 1352 - 1355

23
[ 4393-06-0 ]
[ 100-66-3 ]
[ 35856-80-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With [Ir2(COD)2(SnCl3)2(Cl)2(μ-Cl)2]; In 1,2-dichloro-ethane; at 80℃; for 0.5h;Inert atmosphere;	General procedure: A 10 mL Schlenk flask equipped with a magnetic bar was charged with [Ir(μ-Cl)(COD)Cl(SnCl3)]2 (0.005 mmol), anisole (1.5 mmol), cinnamyl alcohol 1a (0.5 mmol), and 1,2-dichloroethane (2 mL). The flask was degassed, flushed with argon and placed in a constant temperature bath at 80 C. The reaction was allowed to continue at 80 C, and monitored by TLC. After completion, solvent was removed under reduced pressure and the mixture was subjected to column chromatography over silica gel (eluent: gradient mixture of EtOAc/pet. ether) to afford the allylic product 2a in 95% isolated yield.

Reference： [1]Tetrahedron,2012,vol. 68,p. 3776 - 3785

24
[ 4393-06-0 ]
[ 104-94-9 ]
4-methoxy-N-[(2E)-3-phenylprop-2-en-1-yl]aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With dichloro[9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene]palladium(II); In isopropyl alcohol; at 20℃; for 12h;Inert atmosphere;	General procedure: General procedure for amination of allylic alcoholsAllylic alcohols 1 (0.4 mmol), Pd(Xantphos)Cl2 (0.02 mmol, 5 mol%), amines 2(0.6 mmol) and 2-PrOH (1.5 mL) were added to a 25 mL flame-dried Young-typetube under nitrogen atmosphere. The mixture was stirred at room temperature for 12hrs. After concentrated under reduced pressure, the residue was purified by flashcolumn chromatography on silica gel and eluted with EtOAc/PE (1/100-1/1) to affordthe desired product 3.

Reference： [1]ChemSusChem,2012,vol. 5,p. 2039 - 2044
[2]Synlett,2014,vol. 25,p. 2781 - 2786

25
[ 4393-06-0 ]
[ 57294-86-7 ]

Yield	Reaction Conditions	Operation in experiment
89%	With trimethylsilylazide; boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20℃;Inert atmosphere;	General procedure: To the solution of diol(0.84 mmol) in anhydrous CH2Cl2 (15 mL) was added TMSN3 (1.26 mmol), followed by BF3 Et2O (20 mol %) at 0 C. The reaction mixture was stirred at room temperature for complete consumption of the starting material (see Table 1). The reaction mixture was diluted with aq sat. NaHCO3 solution (10 mL) and extracted with CH2Cl2 (2 15 mL). The organic layer was dried over anhydrous Na2SO4, concentrated under vacuum and purified by silica gel column chromatography with ethylacetate/hexane (1:9) as an eluent to furnish the allylic azide.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2382 - 2385

26
[ 221044-05-9 ]
[ 4393-06-0 ]
[ 1446415-22-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With silver hexafluoroantimonate; at 20℃; for 24h;	To the polyethylene glycol-400 catalyst system obtained in Example 13 was added 1 mmol of N-pyrimidine indole and 2 mmol of 1-phenylpropen-1-ol, and the mixture was stirred at room temperature for 24 hours. The progress of the reaction was monitored by TLC. After completion, add ether to extract three times. The obtained polyethylene glycol-400 catalytic system was reused. It was put into the next experiment. The ether solution was combined and concentrated, and separated by column chromatography to obtain 285 mg of light yellow oily liquid with a yield of 87. %, the structural formula of the resulting product is as follows, the resulting polyethylene glycol-400 catalytic system is reused and put into the next experiment:
70%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; In water; at 80℃; for 12h;Schlenk technique; Green chemistry;	General procedure: Heterocycles 1 (0.2mmol, 1.0 equiv), allylic alcohols 2 (0.4 mmol, 2.0 equiv), [Cp*RhCl2]2 (2.5mol %), AgSbF6 (0.02mmol, 10mol %) and H2O (2mL) were charged into a Schlenk tube under air. The reaction mixture was stirred for 12hat 80C. After the reaction was complete, the mixture was extracted with CH2Cl2 three times. The combined organic layer was dried with anhydrous Na2SO4 and evaporated in vacuum. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate as the eluent to give the pure product 3.

Reference： [1]Patent: CN111039927,2020,A .Location in patent: Paragraph 0054; 0117-0121
[2]Chemical Communications,2013,vol. 49,p. 6489 - 6491
[3]Tetrahedron,2018,vol. 74,p. 7364 - 7371

27
[ 96-76-4 ]
[ 4393-06-0 ]
[ 59895-54-4 ]

Yield	Reaction Conditions	Operation in experiment
74%	With bis[(trifluoromethanesulfonyl)imidate]-2-(dicyclohexyl(2’,6’-dimethoxybiphenyl))phosphine gold(I); In toluene; at 60℃; for 41h;	2-Methyl-1-phenylprop-2-en-1-ol (21, 15.2 mg, 113 μmol) and the 2,4-di-tert-butylphenol (5j, 115 mg, 559 μmol) were dissolved in toluene (0.23 mL). PPh3AuNTf2 (as the 2:1 toluene adduct) (4.2 mg, 5.7 μmol) was added to the resulting solution. The reaction was allowed to stir at 60 C for 41 hours. The reaction was then filtered over a plug of silica, using diethyl ether as eluent. The crude product was purified using column chromatography, using a gradient eluent system of 50:1 hexane:diethyl ether to 9:1 hexane:diethyl ether. Product 9v was obtained as a yellow oil (27.1 mg, 84.0 μmol, 74%).νmax/cm-1 3525, 2955, 2905, 2868, 1479, 1448, 1362, 1215, 1199, 972, 878, 755, 692.δH (300 MHz, CDCl3) 7.43-7.25 (6H, m, Ph-H and Ar-H), 7.07 (1H, d, J 2.5 Hz, Ar-H), 6.63 (1H, d, J 15.9 Hz, =CHPh), 6.42 (1H, dt, J 15.9 Hz, 6.5, =CH), 5.13 (1H, s, OH), 3.60 (2H, dd, J 6.5, 1.3 Hz, CH2), 1.44 (9H, s, C(CH3)3), 1.34 (9H, s, C(CH3)3).δC (75 MHz, CDCl3) 151.4 (C), 142.7 (C), 136.8 (C), 136.1 (C), 132.1 (CH), 128.7 (CH), 128.1 (CH), 127.7 (CH), 126.5 (CH), 125.2 (CH), 124.6 (C), 123.0 (CH), 36.1 (CH2), 35.0 (C), 34.4 (C), 31.8 (CH3), 30.0 (CH3).Found (APCI+) [M + NH4]+ 340.2630, C23H34ON requires 340.2635.

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1797 - 1806

28
[ 4837-90-5 ]
[ 4393-06-0 ]
[ 1620878-65-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sulfuric acid; In water; acetonitrile; at 50℃; for 5h;Inert atmosphere; Schlenk technique;	General procedure: A N2 purged flame-dried Schlenk tube containing indole 1(0.200 mmol), [Ir(COD)Cl]2 (0.004mmol), were added successively CH3CN (1 mL), allylic alcohol 2(0.200 mmol) and H2SO4(1 M inH2O)(0.010 mmol) via syringe. The reaction mixture was stirred at 50 C for 5 h. After thereaction was complete, the solvent was removed under reduced pressure. The ratio ofregioisomers(branched/linear) was determined by 1H NMR of the crude reaction mixture. Thecrude residue was purified by flash column silica gel chromatography (petroleum ether/ ethylacetate: 95:5 to 90:10) to yield the product 3.

Reference： [1]Synthesis,2014,vol. 46,p. 1717 - 1724

29
[ 399-52-0 ]
[ 4393-06-0 ]
[ 1620878-66-1 ]

Yield	Reaction Conditions	Operation in experiment
84%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sulfuric acid; In water; acetonitrile; at 50℃; for 5h;Inert atmosphere; Schlenk technique;	General procedure: A N2 purged flame-dried Schlenk tube containing indole 1(0.200 mmol), [Ir(COD)Cl]2 (0.004mmol), were added successively CH3CN (1 mL), allylic alcohol 2(0.200 mmol) and H2SO4(1 M inH2O)(0.010 mmol) via syringe. The reaction mixture was stirred at 50 C for 5 h. After thereaction was complete, the solvent was removed under reduced pressure. The ratio ofregioisomers(branched/linear) was determined by 1H NMR of the crude reaction mixture. Thecrude residue was purified by flash column silica gel chromatography (petroleum ether/ ethylacetate: 95:5 to 90:10) to yield the product 3.

Reference： [1]Synthesis,2014,vol. 46,p. 1717 - 1724

30
[ 10075-50-0 ]
[ 4393-06-0 ]
[ 1046157-56-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sulfuric acid; In water; acetonitrile; at 50℃; for 5h;Inert atmosphere; Schlenk technique;	General procedure: A N2 purged flame-dried Schlenk tube containing indole 1(0.200 mmol), [Ir(COD)Cl]2 (0.004mmol), were added successively CH3CN (1 mL), allylic alcohol 2(0.200 mmol) and H2SO4(1 M inH2O)(0.010 mmol) via syringe. The reaction mixture was stirred at 50 C for 5 h. After thereaction was complete, the solvent was removed under reduced pressure. The ratio ofregioisomers(branched/linear) was determined by 1H NMR of the crude reaction mixture. Thecrude residue was purified by flash column silica gel chromatography (petroleum ether/ ethylacetate: 95:5 to 90:10) to yield the product 3.

Reference： [1]Synthesis,2014,vol. 46,p. 1717 - 1724

31
[ 1006-94-6 ]
[ 4393-06-0 ]
[ 1046157-54-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sulfuric acid; In water; acetonitrile; at 50℃; for 5h;Inert atmosphere; Schlenk technique;	General procedure: A N2 purged flame-dried Schlenk tube containing indole 1(0.200 mmol), [Ir(COD)Cl]2 (0.004mmol), were added successively CH3CN (1 mL), allylic alcohol 2(0.200 mmol) and H2SO4(1 M inH2O)(0.010 mmol) via syringe. The reaction mixture was stirred at 50 C for 5 h. After thereaction was complete, the solvent was removed under reduced pressure. The ratio ofregioisomers(branched/linear) was determined by 1H NMR of the crude reaction mixture. Thecrude residue was purified by flash column silica gel chromatography (petroleum ether/ ethylacetate: 95:5 to 90:10) to yield the product 3.

Reference： [1]Synthesis,2014,vol. 46,p. 1717 - 1724

32
[ 4393-06-0 ]
[ 614-96-0 ]
[ 1164108-87-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sulfuric acid; In water; acetonitrile; at 50℃; for 5h;Inert atmosphere; Schlenk technique;	General procedure: A N2 purged flame-dried Schlenk tube containing indole 1(0.200 mmol), [Ir(COD)Cl]2 (0.004mmol), were added successively CH3CN (1 mL), allylic alcohol 2(0.200 mmol) and H2SO4(1 M inH2O)(0.010 mmol) via syringe. The reaction mixture was stirred at 50 C for 5 h. After thereaction was complete, the solvent was removed under reduced pressure. The ratio ofregioisomers(branched/linear) was determined by 1H NMR of the crude reaction mixture. Thecrude residue was purified by flash column silica gel chromatography (petroleum ether/ ethylacetate: 95:5 to 90:10) to yield the product 3.

Reference： [1]Synthesis,2014,vol. 46,p. 1717 - 1724

33
[ 95-20-5 ]
[ 4393-06-0 ]
[ 1164108-93-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sulfuric acid; In water; acetonitrile; at 50℃; for 5h;Inert atmosphere; Schlenk technique;	General procedure: A N2 purged flame-dried Schlenk tube containing indole 1(0.200 mmol), [Ir(COD)Cl]2 (0.004mmol), were added successively CH3CN (1 mL), allylic alcohol 2(0.200 mmol) and H2SO4(1 M inH2O)(0.010 mmol) via syringe. The reaction mixture was stirred at 50 C for 5 h. After thereaction was complete, the solvent was removed under reduced pressure. The ratio ofregioisomers(branched/linear) was determined by 1H NMR of the crude reaction mixture. Thecrude residue was purified by flash column silica gel chromatography (petroleum ether/ ethylacetate: 95:5 to 90:10) to yield the product 3.

Reference： [1]Synthesis,2014,vol. 46,p. 1717 - 1724
[2]Chemistry - A European Journal,2018,vol. 24,p. 7964 - 7969

34
[ 948-65-2 ]
[ 4393-06-0 ]
[ 1164108-91-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sulfuric acid; In water; acetonitrile; at 50℃; for 5h;Inert atmosphere; Schlenk technique;	General procedure: A N2 purged flame-dried Schlenk tube containing indole 1(0.200 mmol), [Ir(COD)Cl]2 (0.004mmol), were added successively CH3CN (1 mL), allylic alcohol 2(0.200 mmol) and H2SO4(1 M inH2O)(0.010 mmol) via syringe. The reaction mixture was stirred at 50 C for 5 h. After thereaction was complete, the solvent was removed under reduced pressure. The ratio ofregioisomers(branched/linear) was determined by 1H NMR of the crude reaction mixture. Thecrude residue was purified by flash column silica gel chromatography (petroleum ether/ ethylacetate: 95:5 to 90:10) to yield the product 3.

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 7964 - 7969
[2]Synthesis,2014,vol. 46,p. 1717 - 1724

35
[ 603-76-9 ]
[ 4393-06-0 ]
[ 1164108-90-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sulfuric acid; In water; acetonitrile; at 50℃; for 5h;Inert atmosphere; Schlenk technique;	General procedure: A N2 purged flame-dried Schlenk tube containing indole 1(0.200 mmol), [Ir(COD)Cl]2 (0.004mmol), were added successively CH3CN (1 mL), allylic alcohol 2(0.200 mmol) and H2SO4(1 M inH2O)(0.010 mmol) via syringe. The reaction mixture was stirred at 50 C for 5 h. After thereaction was complete, the solvent was removed under reduced pressure. The ratio ofregioisomers(branched/linear) was determined by 1H NMR of the crude reaction mixture. Thecrude residue was purified by flash column silica gel chromatography (petroleum ether/ ethylacetate: 95:5 to 90:10) to yield the product 3.

Reference： [1]Synthesis,2014,vol. 46,p. 1717 - 1724

36
[ 16096-33-6 ]
[ 4393-06-0 ]
[ 1620878-67-2 ]

Yield	Reaction Conditions	Operation in experiment
61%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sulfuric acid; In water; acetonitrile; at 50℃; for 5h;Inert atmosphere; Schlenk technique;	General procedure: A N2 purged flame-dried Schlenk tube containing indole 1(0.200 mmol), [Ir(COD)Cl]2 (0.004mmol), were added successively CH3CN (1 mL), allylic alcohol 2(0.200 mmol) and H2SO4(1 M inH2O)(0.010 mmol) via syringe. The reaction mixture was stirred at 50 C for 5 h. After thereaction was complete, the solvent was removed under reduced pressure. The ratio ofregioisomers(branched/linear) was determined by 1H NMR of the crude reaction mixture. Thecrude residue was purified by flash column silica gel chromatography (petroleum ether/ ethylacetate: 95:5 to 90:10) to yield the product 3.

Reference： [1]Synthesis,2014,vol. 46,p. 1717 - 1724

37
[ 3377-71-7 ]
[ 4393-06-0 ]
[ 1620878-68-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sulfuric acid; In water; acetonitrile; at 50℃; for 5h;Inert atmosphere; Schlenk technique;	General procedure: A N2 purged flame-dried Schlenk tube containing indole 1(0.200 mmol), [Ir(COD)Cl]2 (0.004mmol), were added successively CH3CN (1 mL), allylic alcohol 2(0.200 mmol) and H2SO4(1 M inH2O)(0.010 mmol) via syringe. The reaction mixture was stirred at 50 C for 5 h. After thereaction was complete, the solvent was removed under reduced pressure. The ratio ofregioisomers(branched/linear) was determined by 1H NMR of the crude reaction mixture. Thecrude residue was purified by flash column silica gel chromatography (petroleum ether/ ethylacetate: 95:5 to 90:10) to yield the product 3.

Reference： [1]Synthesis,2014,vol. 46,p. 1717 - 1724

38
[ 862906-97-6 ]
[ 4393-06-0 ]
C₂₈H₂₇NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
> 99%	With palladium diacetate; triphenylphosphine; benzoic acid; In toluene; at 60℃; for 12h;Schlenk technique; Molecular sieve; Inert atmosphere;	General procedure: To a flame-dried Schlenk tube charged with 4 Å MS (50 mg/0.1 mmol) and a magnetic stir bar was added 3-aryloxindoles 1 (0.1 mmol), allylic alcohol 2 (0.2 mmol), Pd(OAc)2 (3.0-10 mol%), Ph3P (3.0-10 mol%), and PhCOOH (3.0-10 mol%) in dry toluene (0.5 mL). The resulting suspension was stirred at the specified temperature under argon for 12 h. Upon completion of the reaction (monitored by TLC), the reaction mixture was diluted with EtOAc and then quenched with sat. aq NH4Cl. The aqueous layer was extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered, concentrated in vacuo, and purified by flash chromatography to afford pure products 3.

Reference： [1]Synlett,2014,vol. 25,p. 2149 - 2154

39
[ 4393-06-0 ]
[ 98180-43-9 ]
(E)-N,N-bis(4-methylbenzyl)-3-phenylprop-2-en-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With dichloro[9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene]palladium(II); In isopropyl alcohol; at 20℃; for 12h;Inert atmosphere;	General procedure: General procedure for amination of allylic alcoholsAllylic alcohols 1 (0.4 mmol), Pd(Xantphos)Cl2 (0.02 mmol, 5 mol%), amines 2(0.6 mmol) and 2-PrOH (1.5 mL) were added to a 25 mL flame-dried Young-typetube under nitrogen atmosphere. The mixture was stirred at room temperature for 12hrs. After concentrated under reduced pressure, the residue was purified by flashcolumn chromatography on silica gel and eluted with EtOAc/PE (1/100-1/1) to affordthe desired product 3.