Hydrosilylation of aldehydes and ketones catalyzed by [Ph3P(CuH)]6

被引：83

作者：

Lipshutz, BH ^{[1
]}

Chrisman, W ^{[1
]}

Noson, K ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2001年 / 624卷 / 1-2期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

cooper hydride; hydrosilylation; silyl ethers; selective reductions;

D O I：

10.1016/S0022-328X(00)00903-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Exposure of an aldehyde or ketone to less than or equal to 5 mol% (in copper) of Stryker's reagent [Ph3P(CuH)](6) in the presence of one of several silanes affords the corresponding protected alcohol in high yields. Aldehydes can be cleanly reduced in the presence of ketones. (C) 2001 Elsevier Science B.V, AH rights reserved.

引用

页码：367 / 371

页数：5

共 21 条

[1] CHEMOSELECTIVE CARBONYL REDUCTION MEDIATED BY LOW-VALENT TITANIUM [J].

ADAMS, CM ;

SCHEMENAUR, JE .

SYNTHETIC COMMUNICATIONS, 1990, 20 (15) :2359-2364

[2]

Barrero AF, 2000, SYNLETT, P197

[3] Highly chemoselective catalytic hydrogenation of unsaturated ketones and aldehydes to unsaturated alcohols using phosphine-stabilized copper(I) hydride complexes [J].

Chen, JX ;

Daeuble, JF ;

Brestensky, DM ;

Stryker, JFM .

TETRAHEDRON, 2000, 56 (15) :2153-2166

[4] Phosphine effects in the copper(I) hydride-catalyzed hydrogenation of ketones and regioselective 1,2-reduction of α,β-unsaturated ketones and aldehydes.: Hydrogenation of decalin and steroidal ketones and enones [J].

Chen, JX ;

Daeuble, JF ;

Stryker, JM .

TETRAHEDRON, 2000, 56 (18) :2789-2798

[5] CONJUGATE ADDITION OF THE PHENYLDIMETHYLSILYL GROUP TO ALPHA-BETA-UNSATURATED CARBONYL-COMPOUNDS USING A SILYLZINCATE IN-PLACE OF THE SILYLCUPRATE [J].

CRUMP, RANC ;

FLEMING, I ;

URCH, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (06) :701-706

[6]

FLEMING I, 1994, ORGANOCOPPER REAGENT, P257

[7] FLUORIDE-ION CATALYZED REDUCTION OF ALDEHYDES AND KETONES WITH HYDROSILANES - SYNTHETIC AND MECHANISTIC ASPECTS AND AN APPLICATION TO THE THREO-DIRECTED REDUCTION OF ALPHA-SUBSTITUTED ALKANONES [J].

FUJITA, M ;

HIYAMA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5405-5415

[8]

GREENE TW, 1991, PROTECTIVE GROUPS OR

[9] VIBRATION-SPECTRA, NORMAL-COORDINATE ANALYSIS AND SYNTHESIS OF TERT-BUTYLSILANES (T)BUSIX(3), X=H, D, F, CL, BR, I [J].

HASSLER, K ;

WEIDENBRUCH, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 465 (1-2) :127-135

[10] Alcoholysis and carbonyl hydrosilylation reactions using a polymer-supported trialkylsilane [J].

Hu, YH ;

Porco, JA .

TETRAHEDRON LETTERS, 1998, 39 (18) :2711-2714

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