Reduction of Carbonyl to Methylene: Organosilane-Ga(OTf)3 as an Efficient Reductant System

被引：13

作者：

Prakash, G. K. Surya ^{[1
,2
]}

Do, Clement ^{[1
,2
]}

Mathew, Thomas ^{[1
,2
]}

Olah, George A. ^{[1
,2
]}

机构：

[1] Univ So Calif, Loker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA

[2] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA

来源：

CATALYSIS LETTERS | 2011年 / 141卷 / 04期

关键词：

Sustainable development; Organosilanes; Gallium triflate; Carbonyl reduction; Hydrosilylation; NICKEL-ALUMINUM ALLOY; GALLIUM(III) TRIFLATE; TRIFLUOROACETIC-ACID; SODIUM-BOROHYDRIDE; IONIC HYDROGENATION; ARYL ALDEHYDES; 3-BICYCLOOCTANONES; SELECTIVE REDUCTION; SILANE REDUCTIONS; SYNTHETIC METHODS;

D O I：

10.1007/s10562-011-0551-0

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Direct carbonyl reduction to methylene has been achieved by mild reductant system obtained from the combination of organosilane and gallium (III) trifluoromethanesulfonate {Ga(OTf)(3)}, a water tolerant, recyclable, catalyst. Among a series of organosilanes studied, dimethylchlorosilane (Me2SiHCl, DMCS) showed the highest efficiency. Both aromatic and aliphatic ketones were effectively reduced to the corresponding methylene products with high functional groups tolerance, under very mild conditions in a relatively short period of time with good to excellent yields.

引用

页码：507 / 511

页数：5

共 56 条

[1]

Augustine R.L., 1965, CATALYTIC HYDROGENAT

[2] Fused carbon rings Part IV Further investigation of 0 3 3-bicyclooctanones in relation to the strain theory [J].

Barrett, JW ;

Linstead, RP .

JOURNAL OF THE CHEMICAL SOCIETY, 1935, :436-442

[3]

BLACKWELL J, 1961, J CHEM SOC, P1405

[4]

BREUER E, 1967, TETRAHEDRON LETT, V20, P1849

[5] HYDROGENOLYSES WITH CHLOROALUMINUM HYDRIDES .4. SATURATED + HOMOBENZYLIC ALCHOLS [J].

BREWSTER, JH ;

HOPPS, HB ;

OSMAN, SF ;

BAYER, HO .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (01) :121-&

[6] REDUCTION OF ALPHA-BETA-UNSATURATED KETONES WITH LITHIUM ALUMINIUM HYDRIDE AND ALUMINIUM CHLORIDE [J].

BROOME, J ;

BROWN, BR ;

ROBERTS, A ;

WHITE, AMS .

JOURNAL OF THE CHEMICAL SOCIETY, 1960, (MAR) :1406-1408

[7] Rapid defunctionalization of carbonyl group to methylene with polymethylhydrosiloxane-B(C6F5)3 [J].

Chandrasekhar, S ;

Reddy, CR ;

Babu, BN .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :9080-9082

[8]

Choi J, 2005, B KOREAN CHEM SOC, V26, P343

[9]

Clark JH, 2005, GREEN SEPARATION PROCESSES: FUNDAMENTALS AND APPLICATIONS, P3

[10]

CLEMMENSEN E, 1913, CHEM BER, V46, P1837

← 1 2 3 4 5 6 →