Ligand-dependent scope and divergent mechanistic behavior in nickel-catalyzed reductive couplings of aldehydes and alkynes

被引：208

作者：

Mahandru, GM ^{[1
]}

Liu, G ^{[1
]}

Montgomery, J ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 12期

关键词：

D O I：

10.1021/ja049644n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new procedure for catalytic reductive coupling of aldehydes and alkynes has been developed. The procedure uses Ni(COD)2 with an imidazolium carbene ligand as the catalyst and triethylsilane as the reducing agent. A crossover deuterium-labeling experiment illustrated that variants involving trialkyl phosphines and imidazolium carbene ligands with a nickel catalyst proceed by different mechanisms. Copyright © 2004 American Chemical Society.

引用

收藏

页码：3698 / 3699

页数：2

相关论文

共 27 条

[1] LOW-COORDINATE CARBENE COMPLEXES OF NICKEL(0) AND PLATINUM(0) [J].

ARDUENGO, AJ ;

GAMPER, SF ;

CALABRESE, JC ;

DAVIDSON, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4391-4394

[2] TITANIUM-CATALYZED REDUCTIVE CYCLIZATION OF DELTA,EPSILON-UNSATURATED KETONES AND ALDEHYDES [J].

CROWE, WE ;

RACHITA, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (25) :6787-6788

[3] Unusual reactivity of molecular oxygen with π-allylnickel(N-heterocyclic carbene) chloride complexes [J].

Dible, BR ;

Sigman, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (04) :872-873

[4]

Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO

[5]

2-Y

[6] Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes [J].

Huang, WS ;

Chan, J ;

Jamison, TF .

ORGANIC LETTERS, 2000, 2 (26) :4221-4223

[7] First catalytic reductive coupling of 1,3-diynes to carbonyl partners: A new regio- and enantioselective C-C bond forming hydrogenation [J].

Huddleston, RR ;

Jang, HY ;

Krische, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11488-11489

[8] CATALYTIC EFFECT OF NICKEL(II) CHLORIDE AND PALLADIUM(II) ACETATE ON CHROMIUM(II)-MEDIATED COUPLING REACTION OF IODO OLEFINS WITH ALDEHYDES [J].

JIN, H ;

UENISHI, J ;

CHRIST, WJ ;

KISHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (18) :5644-5646

[9] Conjugate reduction of α,β-unsaturated carbonyl compounds catalyzed by a copper carbene complex [J].

Jurkauskas, V ;

Sadighi, JP ;

Buchwald, SL .

ORGANIC LETTERS, 2003, 5 (14) :2417-2420

[10] Mechanistic studies of palladium(II)-catalyzed hydrosilation and dehydrogenative silation reactions [J].

LaPointe, AM ;

Rix, FC ;

Brookhart, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (05) :906-917