Cobalt Carbonyl-Based Catalyst for Hydrosilylation of Carboxamides

被引：67

作者：

Dombray, Thomas ^{[1
]}

Helleu, Camille ^{[1
]}

Darcel, Christophe ^{[1
]}

Sortais, Jean-Baptiste ^{[1
]}

机构：

[1] Univ Rennes 1, Inst Sci Chim Rennes Team Organometall Mat & Cata, Ctr Catalysis & Green Chem, UMR CNRS 6226, F-35042 Rennes, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 17期

关键词：

amides; amines; cobalt; hydrosilylation; reduction; CARBOXYLIC-ACID DERIVATIVES; ASYMMETRIC HYDROSILYLATION; TERTIARY-AMINES; ENANTIOSELECTIVE HYDROSILYLATION; EFFICIENT HYDROSILYLATION; SELECTIVE REDUCTION; SECONDARY AMIDES; SILANE REDUCTION; IRON; COMPLEX;

D O I：

10.1002/adsc.201300664

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The cobalt carbonyl [Co-2(CO)(8)] complex is employed as a useful catalyst for the reduction of tertiary amides to the corresponding tertiary amines using 1,1,3,3-tetramethyldisiloxane (TMDS) and poly(methylhydrosiloxane) (PMHS) as silane reagents under thermal (100 degrees C) or photo-assisted conditions (UV, 350nm at room temperature). Of particular interest, a low catalytic amount (0.5mol%) of [Co-2(CO)(8)] is used to perform the reaction with 2.2equiv. of PMHS at 100 degrees C for 3h. This reaction is the first example of a cobalt-catalyzed hydrosilylation of amides.

引用

收藏

页码：3358 / 3362

页数：5

相关论文

共 65 条

[1]

Addis, 2011, ANGEW CHEM, V123, P6128

[2] Selective Reduction of Carboxylic Acid Derivatives by Catalytic Hydrosilylation [J].

Addis, Daniele ;

Das, Shoubhik ;

Junge, Kathrin ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) :6004-6011

[3] N-Heterocyclic Carbene Ligands and Iron: An Effective Association for Catalysis [J].

Bezier, David ;

Sortais, Jean-Baptiste ;

Darcel, Christophe .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) :19-33

[4] Iron-Catalyzed Hydrosilylation of Esters [J].

Bezier, David ;

Venkanna, Gopaladasu T. ;

Castro, Luis C. Misal ;

Zheng, Jianxia ;

Roisnel, Thierry ;

Sortais, Jean-Baptiste ;

Darcel, Christophe .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (10) :1879-1884

[5] Well-Defined Cyclopentadienyl NHC Iron Complex as the Catalyst for Efficient Hydrosilylation of Amides to Amines and Nitriles [J].

Bezier, David ;

Venkanna, Gopaladasu T. ;

Sortais, Jean-Baptiste ;

Darcel, Christophe .

CHEMCATCHEM, 2011, 3 (11) :1747-1750

[6] Hydrosilylation of Aldehydes and Ketones Catalyzed by an N-Heterocyclic Carbene-Nickel Hydride Complex under Mild Conditions [J].

Bheeter, Linus P. ;

Henrion, Mickael ;

Brelot, Lydia ;

Darcel, Christophe ;

Chetcuti, Michael J. ;

Sortais, Jean-Baptiste ;

Ritleng, Vincent .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (14-15) :2619-2624

[7]

Bower, 1996, ANGEW CHEM, V108, P1662

[8] A mild general procedure for the one-pot conversion of amides to aldehydes [J].

Bower, S ;

Kreutzer, KA ;

Buchwald, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14) :1515-1516

[9] MECHANISM OF A COBALT(III)-CATALYZED OLEFIN HYDROSILATION REACTION - DIRECT EVIDENCE FOR A SILYL MIGRATION PATHWAY [J].

BROOKHART, M ;

GRANT, BE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (06) :2151-2156

[10] ASYMMETRIC CATALYSIS .75. ENANTIOSELECTIVE HYDROSILYLATION OF ACETOPHENONE WITH PYRIDINYLOXAZOLINE COBALT(I) COMPLEXES AS CATALYSTS [J].

BRUNNER, H ;

AMBERGER, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 417 (03) :C63-C65

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