Selective Reduction of Carboxylic Acids to Aldehydes Catalyzed by B(C6F5)3

被引：88

作者：

Bezier, David ^{[1
]}

Park, Sehoon ^{[1
]}

Brookhart, Maurice ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 03期

基金：

美国国家科学基金会;

关键词：

ONE-POT CONVERSION; CHEMOSELECTIVE CONVERSION; ORGANIC-COMPOUNDS; METHYL SULFIDE; HYDROGENATION; CHLORIDE; HYDRIDE; KETONES; HYDROSILATION;

D O I：

10.1021/ol303296a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

B(C6F5)(3) efficiently catalyzes hydrosilylation of aliphatic and aromatic carboxylic acids to produce disilyl acetals under mild conditions. Catalyst loadings can be as low as 0.05 mol %, and bulky tertiary silanes are favored to give selectively the acetals. Acidic workup of the disilyl acetals results in the formation of aldehydes in good to excellent yields.

引用

页码：496 / 499

页数：4

共 38 条

[1]

Bajracharya G. B., 2004, SYNTHESIS-STUTTGART, V2004, P308

[2] SYNTHESIS OF ALDEHYDES AND SECONDARY AMINES FROM CARBOXYLIC ACIDS VIA IMINES [J].

BEDENBAUGH, AO ;

BEDENBAUGH, JH ;

BERBIN, WA ;

ADKINS, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (19) :5774-+

[3] EXCEPTIONALLY FACILE REDUCTION OF ACYCLIC AND ALICYCLIC CARBOXYLIC-ACIDS TO ALDEHYDES BY THEXYLCHLOROBORANE DIMETHYL SULFIDE [J].

BROWN, HC ;

CHA, JS ;

NAZER, B ;

YOON, NM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (25) :8001-8002

[4] SELECTIVE REDUCTIONS .39. PARTIAL REDUCTION OF CARBOXYLIC-ACIDS WITH THEXYLCHLOROBORANE-METHYL SULFIDE - A DIRECT AND SIMPLE ALDEHYDE SYNTHESIS [J].

BROWN, HC ;

CHA, JS ;

YOON, NM ;

NAZER, B .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5400-5406

[5] SELECTIVE REDUCTIONS .17. REACTION OF THEXYLBORANE IN TETRAHYDROFURAN WITH SELECTED ORGANIC COMPOUNDS CONTAINING REPRESENTATIVE FUNCTIONAL GROUPS - COMPARISON OF REDUCING CHARACTERISTICS OF DIBORANE AND ITS ALKYL DERIVATIVES [J].

BROWN, HC ;

HEIM, P ;

YOON, NM .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (19) :2942-&

[6] Selective switchable iron-catalyzed hydrosilylation of carboxylic acids [J].

Castro, Luis C. Misal ;

Li, Haoquan ;

Sortais, Jean-Baptiste ;

Darcel, Christophe .

CHEMICAL COMMUNICATIONS, 2012, 48 (85) :10514-10516

[7]

CHA JS, 1987, B KOR CHEM SOC, V8, P313

[8]

CHA JS, 1995, B KOR CHEM SOC, V16, P561

[9] FACILE REDUCTION OF SATURATED AND UNSATURATED CARBOXYLIC-ACIDS AND THEIR SALTS TO ALDEHYDES BY THEXYLBROMOBORANE DIMETHYL SULFIDE [J].

CHA, JS ;

KIM, JE ;

LEE, KW .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :5030-5032

[10] One pot conversion of carboxylic acids to aldehydes with DIBAL-H [J].

Chandrasekhar, S ;

Kumar, MS ;

Muralidhar, B .

TETRAHEDRON LETTERS, 1998, 39 (08) :909-910

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