[ CAS No. 938-16-9 ] {[proInfo.proName]}

Name: 938-16-9|2,2,2-Trimethylacetophenone|97%
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3d Animation Molecule Structure of 938-16-9

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Quality Control of [ 938-16-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 938-16-9 ]

SDS Specification

Alternatived Products of [ 938-16-9 ]

Product Details of [ 938-16-9 ]

CAS No. :	938-16-9	MDL No. :	MFCD00008844
Formula :	C₁₁H₁₄O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OECPUBRNDKXFDX-UHFFFAOYSA-N
M.W :	162.23	Pubchem ID :	70308
Synonyms :

Calculated chemistry of [ 938-16-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.8
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.16 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.26
Log Po/w (XLOGP3) :	3.0
Log Po/w (WLOGP) :	2.92
Log Po/w (MLOGP) :	2.69
Log Po/w (SILICOS-IT) :	2.88
Consensus Log Po/w :	2.75

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.97
Solubility :	0.172 mg/ml ; 0.00106 mol/l
Class :	Soluble
Log S (Ali) :	-3.02
Solubility :	0.154 mg/ml ; 0.000949 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.54
Solubility :	0.0463 mg/ml ; 0.000285 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 938-16-9 ]

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 [ 938-16-9 ]

* 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 [ 938-16-9 ]
Downstream synthetic route of [ 938-16-9 ]

[ 938-16-9 ] Synthesis Path-Upstream 1~5

1
[ 938-16-9 ]
[ 7732-18-5 ]
[ 71-43-2 ]
[ 754-10-9 ]

Reference： [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1909, vol. 148, p. 129

2
[ 938-16-9 ]
[ 75-24-1 ]
[ 2041-37-4 ]

Reference： [1] Journal of the American Chemical Society, 2016, vol. 138, # 32, p. 10132 - 10135

3
[ 938-16-9 ]
[ 61501-04-0 ]

Reference： [1] Tetrahedron, 1965, vol. 21, p. 3263 - 3272
[2] Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 441 - 446
[3] Chemistry - A European Journal, 2005, vol. 11, # 19, p. 5619 - 5624
[4] European Journal of Inorganic Chemistry, 1999, # 6, p. 1029 - 1039

4
[ 938-16-9 ]
[ 540-69-2 ]
[ 61501-04-0 ]

Reference： [1] Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica, 1954, vol. 50, p. 875,884

5
[ 71996-43-5 ]
[ 938-16-9 ]
[ 29671-92-9 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, # 10, p. 1822 - 1828[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 10, p. 2071 - 2077

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Yield	Reaction Conditions	Operation in experiment
100%	With potassium-t-butoxide; hydrogen In hexadeuterobenzene at 20℃; for 12h;
100%	With hydrogen In hexadeuterobenzene at 20℃; for 12h; Alkaline conditions; Cooling with liquid nitrogen;	2.b.3 b) Under an atmosphere of hydrogen gas (1-3 atm) at room temperature, catalytic amounts of the [Ru(P2N2)Y2] or [Ru(P2(NH)2)Y2] complex, together with 3-10 equivalents of KOiPr or KOtBu effectively and readily catalyzed the hydrogenation of the neat ketones or imines to the corresponding alcohol or amine respectively. A general procedure for a catalytic run is as follows: [0074] 1 to 8 g of the substrate, or its solution in 1-2 ml of C6D6, were added under a flow of hydrogen gas to a Schlenk flask containing the desired amount of catalyst and of base (KOiPr or KOtBu). The flask was then cooled to liquid nitrogen temperature, filled with H2 gas, closed and allowed to gradually warm to room temperature to reach an initial H2 pressure of about 3 atm. The mixture was vigorously stirred for 12 to 30 hours. Then, the catalyst was oxidized and precipitated from the alcohols or amines by the addition of hexanes in the air and then removed by filtration through a 5 mm thick pad of silica gel. The hexanes were evaporated to yield the pure alcohol. A sample was dissolved in C6D6 to determine the yield by 1H NMR. Typical conditions and results are listed in Table 5.
100%	With hydrogen In hexadeuterobenzene at 20℃; for 12h; Alkaline conditions; Cooling with liquid nitrogen;	2.b.4 b) Under an atmosphere of hydrogen gas (1-3 atm) at room temperature, catalytic amounts of the [Ru(P2N2)Y2] or [Ru(P2(NH)2)Y2] complex, together with 3-10 equivalents of KOiPr or KOtBu effectively and readily catalyzed the hydrogenation of the neat ketones or imines to the corresponding alcohol or amine respectively. A general procedure for a catalytic run is as follows: [0074] 1 to 8 g of the substrate, or its solution in 1-2 ml of C6D6, were added under a flow of hydrogen gas to a Schlenk flask containing the desired amount of catalyst and of base (KOiPr or KOtBu). The flask was then cooled to liquid nitrogen temperature, filled with H2 gas, closed and allowed to gradually warm to room temperature to reach an initial H2 pressure of about 3 atm. The mixture was vigorously stirred for 12 to 30 hours. Then, the catalyst was oxidized and precipitated from the alcohols or amines by the addition of hexanes in the air and then removed by filtration through a 5 mm thick pad of silica gel. The hexanes were evaporated to yield the pure alcohol. A sample was dissolved in C6D6 to determine the yield by 1H NMR. Typical conditions and results are listed in Table 5.

100%	With potassium-t-butoxide; hydrogen; potassium isopropoxide at 20℃; for 12h;
100%	With potassium-t-butoxide; hydrogen; potassium isopropoxide at 20℃; for 12h;
100%	With potassium fluoride; palladium diacetate; chlorobenzene In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 1h; Inert atmosphere; chemoselective reaction;
99%	With hydrogen In lithium hydroxide monohydrate at 20℃; for 24h; Autoclave;	2.4. General procedure for hydrogenation under hydrogen pressure General procedure: The stainless steel autoclave was charged with the previously prepared aqueous suspension of Col-Ni-CMC Nps (8 mL, from 40 mg of NiCl2·6H2O and 10 mL, from 50 mg of NiCl2·6H2O) for ketone hydrogenation. The appropriate nitro-aromatic ([substrate]/[metal] = 100) in 2 mL of MeOH, was added into the autoclave and dihydrogen was admitted to the system at constant pressure (10 to 40 bars). The mixture was stirred until the reaction was finished. Samples for gas chromatographic analysis were removed from time to time. The residue was extracted with diethyl ether (3 × 25 mL). The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure Pure products were obtained by column chromatography over silica gel using hexane/ethyl acetate as eluent.
99%	With C₉H₈BrMnN₂O₃; potassium-t-butoxide In isopropanol at 30℃; for 16h; Inert atmosphere; Schlenk technique; Glovebox;
99%	With potassium-t-butoxide; hydrogen; C₄₀H₄₉Cl₂FeNO₃PRuS; isopropanol at 60℃; for 16h;	22 In an argon glove box, the complex Ru-(SFC)-L22 (0.01mmol) and α,α-dimethylpropiophenone (162mg, 1mmol) were added to a 5mL hydrogenation flask,dissolvedwithiPrOH (1mL), and thentBuOK (5.6mg ,0.05mmol) solid powder, finally addiPrOH (0.5mL), then put the reaction flask into the hydrogenation kettle, replace the kettle body with hydrogen three times, and then fill it with 50bar H2, React at 50°C for 16h.After the reaction is completed, the hydrogen is released carefully, the solvent is spin-dried under reduced pressure, and the hydrogenated product α,α-dimethylphenylpropanol is purified by silica gel column, a colorless transparent liquid, >99% conversion, >99% yield.
99%	With potassium-t-butoxide; hydrogen; C₄₅H₃₇Cl₄FeNO₃PRuS In isopropanol at 50℃; for 16h; Inert atmosphere; Glovebox;	23 In an argon glove box, the complex Ru-(S,R)-f-ambinol-L1 (9.6mg, 0.01mmol) and α,α-dimethylpropiophenone (162mg, 1mmol) were added to a 5mL hydrogenation bottle Dissolve the inside with iPrOH (1mL), then add tBuOK (5.6mg, 0.05mmol) solid powder to the hydrogenation flask, and finally iPrOH (0.5mL), then put the reaction flask into the hydrogenation kettle, and replace the kettle with hydrogen. After three times, it was filled with 50bar H2 and reacted at 50°C for 16h. After the reaction is completed, the hydrogen is released carefully, the solvent is spin-dried under reduced pressure, and the hydrogenated product α,α-dimethylphenylpropanol is purified by silica gel column, a colorless transparent liquid, >99% conversion, >99% yield.
98%	With copper(II) bis(2,4-pentanedionate); hydrogen In methanol at 90℃; for 20h; Autoclave;
96%	With di-μ-chlorobis-[(η⁶-p-cymene)chlororuthenium(II)]; 2-(2-methyl-2,3-dihydro-1H-perimidin-2-yl)benzene-1,3-diol; anhydrous sodium carbonate; isopropanol; potassium hydroxide In dichloromethane at 90℃; for 12h;	2.4 Transfer hydrogenation of ketones General procedure: A mixture of [(η6-p-cymene)RuCl2]2 (0.030 g, 0.049 mmol), ligand 2 (0.014 g, 0.049 mmol) and sodium carbonate (0.025 g, 0.24 mmol) in dichloromethane (5 mL) was stirred at room temperature for 6 h. After filtering on a small Celite bed the solvent was removed in vacuo to give a brown solid. Freshly distilled i-propanol (5 mL), potassium hydroxide (0.011 g, 0.2 mmol) and the ketone (5.0 mmol) were added. After 12 h stirring at 90 °C the cooled reaction mixture was filtered on Celite and most of unreacted i-propanol was removed in vacuo. To assess the extent of the reduction the integrals of suited signals in 1H NMR spectra (CDCl3) were compared, respectively for the ketone PhCOR and the corresponding alcohol PhCH(OH)R (TOF: 3.7 h-1 for R = Me; 2.6 h-1 for R = i-Pr; 4.1 h-1 for R = t-Bu).
96%	With manganese(I) pentacarbonyl bromide; potassium-t-butoxide; Ethane-1,2-diamine In isopropanol at 80℃; for 3h;	2.1. Representative procedure for transfer hydrogenation reaction ofacetophenone General procedure: To a solution of acetophenone (58 μL, 0.5 mmol) in 2-propanol (0.5 mL) was added a stock solution of manganese pentacarbonyl bromide (0.5 mL, 0.005 mol·L-1; 2.7 mg, 0.010 mmol, in 2 mL 2-propanol)followed, in this order, by a stock solution of ethylenediamine (0.5 mL,0.005 mol·L-1; 1.0 μL, 0.0125 mmol, in 2.5 mL 2-propanol) and tBuOK (0.5 mL, 0.010 mol·L-1; 2.4 mg, 0.020 mmol, in 2 mL 2-propanol). The reaction mixture was stirred for 3 h at 80 °C in an oil bath. The solution was then filtered through a small pad of silica (2 cm in a Pasteur pip-ette). The silica was washed with ethyl acetate. The filtrate was evaporated and the conversion was determined by 1H NMR. The crude residue was then puried by column chromatography (SiO 2 , mixture of petroleum ether/ethyl acetate or dietyl ether as eluent. Enantiomeric excesses were determined by GC analyses performedon GC-2014 (Shimadzu) 2010 apparatus equipped with Supelco beta-DEX 120 column (30 m × 0.25 mm). The determination of the absoluteconguration was done by comparison with (S)-alcohol obtained bykinetic resolution of racemic alcohols with Novozym 435 (CandidaAntarctica Lipase B) and by comparison of the retention times with the literature [32-34].
95%	Stage #1: 2,2-dimethylpropiophenone With nickel(II) acetate tetrahydrate; tricyclohexylphosphine In tetrahydrofuran at 100℃; for 16h; Stage #2: With sodium hydroxide In methanol
94%	With potassium hydroxide; isopropanol at 80 - 85℃; for 20h;
94%	With [Ru(CH₃CN)₃(κ²-o-DPPBS)Cl] In methanol at 60℃; for 15h; Autoclave;
92%	Stage #1: 2,2-dimethylpropiophenone With bis-[N,N′-bis(2,6-(di-isopropyl)phenyl)imidazol-2-ylidene]-(1H-1,2,4-triazol-1-yl)}copper(I) In tetrahydrofuran at 55℃; for 6h; Stage #2: With sodium hydroxide In methanol; lithium hydroxide monohydrate at 25℃; for 1.5h;
91%	With 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In hexadeuterobenzene at 25℃; for 6h; Inert atmosphere; Glovebox; Sealed tube;
89%	With Rhodium trichloride; hydrogen In lithium hydroxide monohydrate at 100℃; for 10h; chemoselective reaction;
87%	With lithium aluminium hydride In diethyl ether
87%	With lithium isopropoxide In isopropanol at 180℃; for 0.5h; microwave irradiation;
85%	With sodium tetrahydridoborate In lithium hydroxide monohydrate; benzene
85%	Stage #1: 2,2-dimethylpropiophenone With n-butyllithium; 1-(2-hydroxyethyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate; ferrous acetate In tetrahydrofuran at 65℃; for 1h; Inert atmosphere; Stage #2: With lithium hydroxide monohydrate; sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 2h; Inert atmosphere;
85%	Stage #1: 2,2-dimethylpropiophenone With glacial acetic acid In acetonitrile at 25℃; for 0.0833333h; Stage #2: In acetonitrile at 25℃; for 12h; Electrochemical reaction;
83%	With tripotassium phosphate tribasic; 1-(4-(dimethylamino)phenyl)ethyl alcohol In 1,4-dioxane at 120℃; for 16h; Inert atmosphere; Sealed tube;
80%	With [Cp*Ir(2,2'-bpyO)(OH)][Na]; hydrogen In lithium hydroxide monohydrate at 30℃; for 12h; Green chemistry;	4.1. General procedure for catalytic hydrogenation of ketones,aldehydes or unsaturated aldehydes General procedure: To an oven-dried 5 mL round-bottom flask were added ketonesor aldehydes or unsaturated aldehydes (1 mmol), cat. 6 (5.5 mg,1 mol %) and H2O (1 mL). Next, vacuum was applied to the flask followedby filling with H2 gas and keeping the flask attached to a balloonfilled with H2 gas. The mixture was heated at 30 °C for 12 h.After completion of the reaction, the mixture was extracted withethyl acetate (5 mL x 3). Then, the ethyl acetate layers were combined, dried with anhydrous sodium sulfate, filtered, and concentratedby evaporation under reduced pressure. The alcohols wereisolated and purified by filtering a hexanes/ethyl acetate (8:1)solution of the crude product through a pad of silica gel. Thenthe solvent was removed under reduced pressure to afford the correspondingproducts. The purity of alcohol products was assessedusing 1H NMR spectroscopy.
78%	With ammonia; lithium perchlorate In N,N-dimethyl-formamide at 20℃; Electrochemical reaction;
76%	With C₁₇H₁₃BrMnN₃O₃; sodium isopropanolate; isopropanol at 90℃; for 3h; Inert atmosphere; Sealed tube;
75%	With Triethoxysilane at 25℃; for 2h;
72%	With [Re(NH{CH₂CH₂P(iPr₂)}₂)(CO)₃]Br; potassium-t-butoxide; hydrogen In toluene at 110℃; for 20h; Inert atmosphere; Glovebox; Autoclave;
72%	With methanol; bis[dichlorido(η⁵-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)]; 6,6′-dihydroxy-2,2′-bipyridine; potassium hydroxide at 60℃; for 24h; Inert atmosphere;
69%	With sodium tetrahydridoborate In lithium hydroxide monohydrate; benzene at 20 - 22℃; for 11.5h; or N-benzylquininium chloride;
69%	With sodium tetrahydridoborate In lithium hydroxide monohydrate; benzene at 20 - 22℃; for 11.5h;
65%	With C₁₅H₁₈BF₃; hydrogen; phosphazene base P₁-t-bu-tris(tetramethylene) In tetrahydrofuran at 75℃; for 40h; Glovebox;
62%	With [RuCl(PPh₃)₂(3-phenylindenyl)]; 1,1,1,3,3,3-hexamethyldisilazane potassium; isopropanol at 89℃; for 14h; Glovebox;
55%	Stage #1: 2,2-dimethylpropiophenone With n-butyllithium; ferrous acetate; 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride In tetrahydrofuran; hexane at 65℃; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; methanol; hexane; lithium hydroxide monohydrate at 20℃; for 3h; Inert atmosphere;
50%	With ethynylmagnesium bromide In tetrahydrofuran at -78℃; for 5h;
41%	With sodium tetrahydridoborate In methanol at 20℃;
17%	With diphenylsilane; [L₂CoBr](PF₆) In acetonitrile for 24h; Glovebox; Reflux;
1%	With 2-(N-morpholino)ethanesulfonic acidbuffer; nadide; isopropanol at 30℃; for 20h; acetone powder of Geotrichum candidum;
	With sodium tetrahydridoborate In lithium hydroxide monohydrate; benzene for 2h;
	With <(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl-1-yl>methyl magnesium chloride In diethyl ether at 20℃; for 1h; asymmetric addition/reduction with Grignard reagents; other Grignard reagents;
	With isopropylmagnesium iodide
	With ethanol; natrium
	With n-propylmagnesium iodide
	With sodium tetrahydridoborate In ethanol Ambient temperature;
	With potassium hydroxide; <Ir(COD)R(-)PPEI>ClO₄; isopropanol; sodium iodide at 83℃; for 1.25h; Yield given;
	With sodium tetrahydridoborate
	With lithium aluminium hydride; diethyl ether
	With tris isopropylate aluminium; isopropanol
	With palladium on activated charcoal; ethanol Hydrogenation;
70 % Spectr.	With ammonium hydroxide; titanium(III) trichloride In methanol at 20 - 25℃; for 0.0833333h;
	With potassium-t-butoxide; hydrogen In <i>tert</i>-butyl alcohol at 210℃;
	With [OsCl₂(dppb)(Pyme)]; sodium isopropanolate; isopropanol at 82℃; for 0.5h; Inert atmosphere;
	Stage #1: 2,2-dimethylpropiophenone With [(Cp*)Rh(Cl)(κ2-3-PiPr2-2-S-indene)]; phenylsilane; lithium tetrakis(pentafluorophenyl)borate In tetrahydrofuran at 20℃; for 5h; Stage #2: With hydrogenchloride In tetrahydrofuran; lithium hydroxide monohydrate; propan-2-one at 0 - 20℃; for 2.5h;
7 %Chromat.	With ethanol; titanium(IV) dioxide at 32℃; for 8h; Inert atmosphere; UV-irradiation;
	With cis-[Ru(6,6'-Me₂bipy)2(H₂O)2](OTf)2; potassium-t-butoxide In isopropanol at 85℃; for 18h; Inert atmosphere;
	With [Ru(p-cymene)(m-CH₂NH₂)Cl]PF₆; potassium-t-butoxide; hydrogen In tetrahydrofuran at 50℃; Inert atmosphere;
	With sodium tetrahydridoborate In methanol Inert atmosphere;
	With hydrogen In tetrahydrofuran at 50℃; for 24h; Autoclave; chemoselective reaction;
	With Ru(Ph2PNHCH2-C4H3O)(η-6-benzene)Cl2; isopropanol; potassium hydroxide at 82℃; for 0.333333h;
	With trans-[OsCl₂(1,1'-bis(diphenylphosphino)ferrocene)(2-aminomethylpyridine)]; sodium isopropanolate; isopropanol at 100℃; for 1h; Inert atmosphere;
	With [1-(aminoethyl)-3-methylimidazol-2-ylidene]-chloro-(η6-p-cymene)ruthenium(II) hexafluorophosphate; potassium-t-butoxide; isopropanol at 75℃; for 8h; Inert atmosphere;
	With [C₁₀H₆N₂{NHPPh₂Ru(η⁶-benzene)Cl₂}₂]; sodium hydroxide In isopropanol for 1h; Reflux; Inert atmosphere;	4.3.4 General procedure for the transfer hydrogenation of ketones General procedure: Typical procedure for the catalytic hydrogen transfer reaction: a solution of complexes [C10H6N2{NHPPh2Ru(η6-benzene)Cl2}2], 1, [C10H6N2{PPh2NHRh(cod)Cl}2], 2 and [C10H6N2{NHPPh2Ir(η5-C5Me5)Cl2}2], 3 (0.005 mmol), NaOH (0.025 mmol) and the corresponding ketone (0.5 mmol) in degassed iso-PrOH (5 mL) were refluxed for 10 min for 1, 1 h for 2 and 3 h for 3. After this period a sample of the reaction mixture was taken off, diluted with acetone and analyzed immediately by GC. Conversions obtained are related to the residual unreacted ketone.
	With sodium tetrahydridoborate In ethanol Inert atmosphere;
	With [Rh((Ph₂P)₂NCH₂-C₄H₃S)(Cp*)Cl]Cl; sodium hydroxide In isopropanol at 82℃; for 24h; Schlenk technique; Inert atmosphere;
	With Rh(COD)(CpFe[η⁵-1,2-C₅H₃(PPh₂)(CH₂S^tBu)])(BF₄); hydrogen; sodium methoxide In isopropanol at 25℃; for 16h; Autoclave; enantioselective reaction;
	With [Ru(Cy₂PNHCH₂-C₄H₃S)(η⁶-benzene)Cl₂]; isopropanol; sodium hydroxide at 82℃; for 6h; Inert atmosphere; Schlenk technique;
	With [Rh(Cy₂PNHCH₂-C₄H₃O)(cod)Cl]; isopropanol; sodium hydroxide at 82℃; for 1.5h; Inert atmosphere; Schlenk technique;	4.2. General procedure for the transfer hydrogenation of ketones General procedure: Typical procedure for the catalytic hydrogen transfer reaction: a solution of complexes [Rh(Cy2PNHCH2-C4H3O)(cod)Cl], (1),[Rh(Cy2PNHCH2-C4H3S)(cod)Cl], (2), [Ir(Cy2PNHCH2-C4H3O)(η5-C5Me5)Cl2], (3) and [Ir(Cy2PNHCH2-C4H3S)(η5-C5Me5)Cl2], (4)(0.005 mmol), NaOH (0.025 mmol) and the corresponding ketone(0.5 mmol) in degassed iso-PrOH (5 mL) were refluxed until the reactions were completed. After this period a sample of the reactionmixture was taken off, diluted with acetone and analyzed immediately by GC. Conversions obtained are related to the residual unreacted ketone.
	With [Ru((Ph₂PO)-C₇H₁₄N₂Cl)(η⁶-p-cymene)Cl₂]Cl; potassium hydroxide In isopropanol at 82℃; for 3h; Inert atmosphere; Schlenk technique;	3.2 Transfer hydrogenation of ketones General procedure: Typical procedure for the catalytic hydrogen transfer reaction: a solution of the complexes [Ru((Ph2PO)-C7H14N2Cl)(η6-arene)Cl2]Cl and [Ru((Ph2PO)-C7H14N2Cl)(η6-arene)Cl2]Cl {arene: benzene 4, 5; p-cymene 6, 7} (0.005 mmol), KOH (0.025 mmol) and the corresponding ketone (0.5 mmol) in degassed 2-propanol (5 mL) was refluxed until the reactions were completed. Then, a sample of the reaction mixture was taken off, diluted with acetone and analyzed immediately by GC. The conversions are related to the residual unreacted ketone. GC analyses were performed a Shimadzu 2010 Plus Gas Chromatograph equipped with a capillary column (5 % biphenyl, 95 % dimethylsiloxane) (30 m×0.32 mm×0.25 μm). The GC parameters for transfer hydrogenation of the ketones were as follows: initial temperature, 50° C; initial time, hold min 1 min; solvent delay, 4.48 min; temperature ramp 15° C/min; final temperature, 270° C, hold min 5 min; final time, 20.67 min; injector port temperature, 200° C; detector temperature, 200° C, injection volume, 2.0 μL
62 %Spectr.	With C₃₆H₁₀₃AlO₄Si₁₄; isopropanol In neat (no solvent) at 80℃; for 24h; Glovebox; Schlenk technique;
	With sodium tetrahydridoborate In ethanol at 0 - 20℃;
	With [(ruthenium(II))3(2-[(diphenylphosphanyl)({2-[(diphenylphosphanyl)oxy]ethyl})amino]-ethyldiphenylphosphinite)(η6-p-cymene)3Cl6]; isopropanol; sodium hydroxide at 82℃; for 1h; Reflux;
	With [(ruthenium(II))3(2-[(diphenylphosphanyl)({2-[(diphenylphosphanyl)oxy]ethyl})amino]-ethyldiphenylphosphinite)(η6-p-cymene)3Cl6]; isopropanol; sodium hydroxide at 82℃; Inert atmosphere; Schlenk technique;
	With sodium tetrahydridoborate In ethanol at 0 - 20℃;
	With [Ru(2,2'-bipyridine)₂(1,5-dihydro-2H-cyclopenta[1,2-b:5,4-b′]dipyridine-2-one)](PF₆)₂; isopropanol; sodium hydroxide at 82℃; for 12h;	2.2 General procedure for the transfer hydrogenation of ketones General procedure: A typical procedure for the catalytic hydrogen transfer reaction was as follows: A solution of the complex [Ru(bpy)2L](PF6)2], NaOH (0.025mmol) and the corresponding ketone (0.5mmol) in degassed iso-Pr-OH (5mL) were refluxed until the completion of the reaction. After this period, a sample of the reaction mixture was taken, diluted with acetone and analyzed immediately by GC. Conversions obtained were related to the residual unreacted ketone. The GC parameters were as follows: initial temperature, 110°C; initial time, 1min; solvent delay, 4.48min; temperature ramp 80°C/min; final temperature, 200°C; final time, 21.13min; injector port temperature, 200°C; detector temperature, 200°C; injection volume, 2.0μL.
	Stage #1: 2,2-dimethylpropiophenone With di-μ-chlorobis-[(η⁶-p-cymene)chlororuthenium(II)]; Boc-L-alanine(2S)-hydroxypropylamide In tetrahydrofuran; ethanol at 40℃; for 0.25h; Inert atmosphere; Stage #2: With potassium-t-butoxide In tetrahydrofuran; ethanol at 40℃; for 24h; Inert atmosphere; enantioselective reaction;
	With di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium; C₃₁H₃₀FePS; hydrogen; sodium methoxide In isopropanol at 27℃; for 5h; Glovebox; Autoclave;
	With RuCl(4-phenyl-2-aminomethylbenzo[h]quinoline-H)(dppp); sodium isopropanolate In propyl alcohol at 82℃; for 0.666667h; Inert atmosphere;
	With sodium tetrahydridoborate In methanol at 20℃; for 1h;
82 %Chromat.	With (4-NHCpr)Triaz(NHP<SUP>i</SUP>Pr<SUB>2</SUB>)<SUB>2</SUB>Mn(CO)<SUB>2</SUB>Br; potassium-t-butoxide; hydrogen In toluene at 80℃; for 24h; Inert atmosphere; Autoclave;
	With C₂₉H₃₆Cl₃IrN₂OP⁽¹⁺⁾*Cl^(1-); isopropanol; sodium hydroxide for 9h; Inert atmosphere; Schlenk technique;	2.2 Transfer hydrogenation of ketones General procedure: Typical procedure for the catalytic hydrogen transfer reaction: a solution of cataysts (1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-yl diphenylphosphinite chloride) (chloro 4-1,5-cyclooctadiene rhodium(I))], 2 or (1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-yl diphenylphosphinite chloride) (dichloro 5-pentamethylcyclopentadienyl iridium(III))], 3 (0.005mmol), NaOH (0.025mmol) and the corresponding ketone (0.5mmol) in degassed 2-propanol (5mL) were refluxed until the reactions were completed. Then, a sample of the reaction mixture was taken off, diluted with acetone and analyzed immediately by GC. The conversions are related to the residual unreacted ketone. GC analyses were performed on a Shimadzu 2010 Plus Gas Chromatograph equipped with capillary column (5% biphenyl, 95% dimethylsiloxane) (30m×0.32mm×0.25μm). The GC parameters for transfer hydrogenation of ketones were as follows; initial temperature, 50°C; initial time, hold min 1min; solvent delay, 4.48min; temperature ramp 15 °C/min; final temperature, 270°C, hold min 5min; final time, 20.67min; injector port temperature, 200°C; detector temperature, 200°C, injection volume, 2.0μL.
	With C₄₇H₄₁ClN₂P₂Ru; sodium isopropanolate; isopropanol In neat (no solvent) at 82℃; for 0.666667h; Inert atmosphere;	23 Example 23 Transfer hydrogenation of ketones. The catalyst (2.5 μηιοΙ) used was dissolved in 2.5 mL of 2-propanol. The ketone (2.0 mmol) was dissolved in 2-propanol and the solution (final volume 19.4 mL) was heated under argon at reflux. By addition of 400 μ of NaO/'Pr (0.1 M, 40 μηιοΙ) in 2-propanol and 200 of the solution containing the catalyst the reduction of the ketone started immediately and the yield was determined by GC after reaction times given in the Table 1 Table 1. Catalytic transfer hydrogenation of ketones (0.1 M) with complexes 13-20 (S/C = 5000- 20000) and NaO/'Pr (2 mol %) in 2-propanol at 82 °C. Conv. Entry Complex Ketone S (M) S/C t (min) (%)a 1 13 23 0.1 10000 2 98 2 14 23 0.1 5000 10 99 3 14 23 0.1 10000 15 99 4 14 23 0.1 20000 15 98 5 14 23 0.2 10000 15 96 6 14 23 0.5 10000 15 93 7 15 23 0.1 10000 2 97 8 15 23 0.1 20000 10 97 9 16 23 0.1 10000 10 96 10 17 23 0.1 10000 10 95 1 1 18 23 0.1 10000 20 93 12 19 23 0.1 10000 10 97 13 20 23 0.1 10000 2 97b 14 17 24 0.1 10000 10 94 15 15 25 0.1 10000 20 99 16 15 26 0.1 10000 40 95 17 18 26 0.1 10000 20 93 18 13 27 0.1 5000 40 99 19 18 27 0.1 5000 14 h 97 20 13 28 0.1 5000 40 99 21 18 28 0.1 5000 14 h 98 22 15 29 0.1 10000 10 99 23 15 30 0.1 10000 10 98 24 17 31 0.1 10000 5 99 25 17 32 0.1 10000 5 99 a The conversion was determined by GC analysis. b ee = 85% (S) The catalysts of this investigation reduce a wide structural variety of ketones. In 2-propanol at reflux and in the presence of NaO/'Pr (2 mol %) the ketones in Table 1 are efficiently reduced via transfer hydrogenation with a S/C ratio up to 20000/1 . The ketones are selected to cover a broad range of structures: alkyl-arylketones 23-27, benzophenone 29 and dialkylketones 28, 30-32. Ketones 27 and 28 having bulky tertBu substituents are reduced with near complete conversion of the substrate. Reduction of C=0 bond of 5-hexen-2-one 30 is entirely chemoselective, without saturation or isomerization of the terminal C=C bond. The use of methyl-benzo[ ?]quinoline or phenyl-benzo[ ?] quinoline ligands allows a fine tuning of catalyst activity and selectivity. The chiral complex 20 containing the (S,R)-JOSIPHOS ligand reduced 23 quantitatively to (S)-1 -phenylethanol in 2 min and with 85 % ee.
	With sodium hydroxide; phenylboronic acid In isopropanol at 82℃;	2.3. Transfer hydrogenation of acetophenone by BL1 and BL2 General procedure: The common procedure for transfer hydrogenation: particular amount of (0.04 mmol) boroncomplex solutions, NaOH (0.05 mmol), and acetophenone (5 mmol) in degassed isoPrOH(5 mL) were reuxed at 82 °C. Samples from the mixture were taken, diluted with acetoneand checked for conversion at dierent time periods. The products were compared with theunreacted acetophenone. GC analyses were applied with a Shimadzu 2010 Plus GasChromatograph having a capillary column (95% dimethyl siloxane and 5% biphenyl)(30 m × 0.32 mm × 0.25 m). The adjusted GC parameters were: initial temperature, 50 °C;solvent delay, 4.48 min; initial time, hold 1 min; nal temperature, 270 °C; hold 5 min; temperatureramp 15 °C min-1; injector port temperature, 200 °C; detector temperature, 200 °C,nal time, 20.67 min, and injection volume, 1.5 L.
	Multi-step reaction with 2 steps 1: sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; C₂₄H₂₃ClCrIrNO₃ / dichloromethane / 2 h / 25 °C / Schlenk technique; Glovebox; Inert atmosphere 2: sodium hydroxide / methanol; lithium hydroxide monohydrate / 12 h / 25 °C / Inert atmosphere
> 90 %Chromat.	Stage #1: 2,2-dimethylpropiophenone With phenylsilane; [(k²-P,N)Mn(N(SiMe₃)₂)] In hexadeuterobenzene at 25℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Stage #2: With sodium hydroxide In hexadeuterobenzene; lithium hydroxide monohydrate for 3h; Inert atmosphere; Glovebox;
	With C₁₅H₁₄Cl₂N₂O₂Ru; sodium isopropanolate; tricyclohexylphosphine In isopropanol at 82℃; for 0.333333h; Inert atmosphere; Schlenk technique;
50 mg	With C₂₈H₂₅BrMnN₂O₃P; potassium-t-butoxide; hydrogen In tert-Amyl alcohol at 100℃; for 20h; Glovebox; Autoclave;
91 %Chromat.	With C₁₈H₂₁BrMnN₃O₃; potassium-t-butoxide; isopropanol at 40℃; for 24h;
	With sodium tetrahydridoborate In tetrahydrofuran; lithium hydroxide monohydrate at 20℃;
	Multi-step reaction with 2 steps 1: C₁₆H₁₁BrMnN₃O₃ / tetrahydrofuran / 3 h / 100 °C / Inert atmosphere; Sealed tube 2: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 20 °C
	With sodium tetrahydridoborate In methanol at 0 - 20℃;	Synthesis of alcohol substrates General procedure: Alcohols (2-3a, 14-15a, 19-22a, 24-25a) were synthesized by reduction ofcorresponding ketones with NaBH4 in MeOH according to the previous report.1Typically, ketone (15 mmol) was dissolved in 100 mL MeOH. Then the solution wascooled to 0 °C in ice bath, followed by slow addition of NaBH4 (5 mmol). The reactionwas kept stirring at 0 °C for 10 min and warmed to room temperature for 1 h to 12 huntil ketone was fully consumed. Then the reaction mixture was concentrated in vacuobefore adding 100 mL saturated aqueous NH4Cl. The aqueous phase was extracted withethyl acetate for three times (3×100 mL). The organic phase was washed with brine,dried with anhydrous Na2SO4, and finally concentrated in vacuo to produce thecorresponding alcohols. Further purification was conducted using gel columnchromatography if necessary.
	With sodium isopropanolate; C₅₀H₄₆N₂O₂P₂Ru In isopropanol at 82℃; for 18h; Inert atmosphere; Schlenk technique;
	With methanol; sodium tetrahydridoborate at 0℃; Schlenk technique; Cooling with ice; Inert atmosphere;
	Multi-step reaction with 2 steps 1: C₂₂H₁₅FeNO₃ / toluene / 12 h / 50 °C / Inert atmosphere; Sealed tube 2: lithium hydroxide monohydrate
	With C₂₄H₃₃BO₂; isopropanol; sodium hydroxide at 82℃; for 18h; Inert atmosphere; Sealed tube;	2.4 General procedure for transfer hydrogenation of ketones with boronate ester catalysts General procedure: The trigonal-planar or tetrahedral catechol boronate ester catalysts (0.005mmol), NaOH (0.025mmol), and the corresponding ketone (0.5mmol) were weighed into a Teflon septum-sealed vial (reaction flask) in an inert atmosphere conditions in degassed isoPrOH (5.0mL), and then a sample of the reaction mixture is taken off, diluted with acetone, and analyzed immediately by GC; conversions obtained are related to the residual unreacted ketone.
	With sodium tetrahydridoborate; ethanol at 0 - 20℃;
	With [dichloro(η4-pentamethylcyclopentadienyl)(1-furan-2-ylethyldiphenylphosphinite)iridium(III)]; potassium hydroxide In isopropanol at 82℃; for 10h;	2.3. General procedure for the transfer hydrogenation of ketones General procedure: A typical procedure for the catalytic hydrogen transfer reaction is given below: a solutionof pre-catalysts (2-5) (0.0025mmol), KOH (0.0125mmol), and the respective ketone(0.5mmol) in degassed 2-propanol (5mL) was refluxed until the reactions were completed.Then, a sample of the reaction mixture was taken off, diluted with acetone, and analyzedimmediately by GC. The conversions are related to the residual unreacted ketone.

Yield	Reaction Conditions	Operation in experiment
88%	With hydroxylamine hydrochloride; sodium acetate In methanol; water Heating;
72%	With pyridine; hydroxylamine hydrochloride at 20℃;
	With ethanol; hydroxylamine

Yield	Reaction Conditions	Operation in experiment
100%	With sodium tetrahydroborate In methanol; ethanol for 2h;
	With yellow ammonium sulfide at 205℃;
	With hydrogenchloride; amalgamated zinc

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