Carbon-carbon bond forming reactions of N-bound transition metal α-cyanocarbanions:: a mechanistic probe for catalytic Michael reactions of nitriles

被引：29

作者：

Naota, T ^{[1
]}

Tannna, A ^{[1
]}

Murahashi, S ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn Sci, Dept Chem, Osaka 5608531, Japan

来源：

CHEMICAL COMMUNICATIONS | 2001年 / 01期

关键词：

D O I：

10.1039/b007517p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Bound alpha -cyanocarbanion complexes Ru+Cp((NCCH-R1))(PPh3)(2) 1 react with electron deficient olefins to afford the conjugate adduct Ru+Cp((NCC-RCHRCRR4)-C-1-C-2-R-3)(PPh3)(2) 2, kinetic studies of which revealed that complex 1-catalyzed Michael reactions of nitriles proceed via transformation of 1 to 2 and subsequent ligand exchange with nitriles.

引用

收藏

页码：63 / 64

页数：2

相关论文

共 23 条

[1]

*CHEM SOC JAP, 1998, 74 ANN M CHEM SOC JA

[2] REACTIONS OF THE CYANOMETHYL COMPLEX (ETA-5-C5H5)RE(NO)(PPH3)(CH2CN) AND YLIDE COMPLEX [(ETA-5-C5H5)RE(NO)(PPH3)(CH2P(PARA-TOL)3)]+PF6- WITH NORMAL-BULI/TMEDA - GENERATION, STEREOSPECIFIC ALKYLATION, AND BASICITY OF TRANSITION-METAL-SUBSTITUTED CARBANIONS AND YLIDES [J].

CROCCO, GL ;

LEE, KE ;

GLADYSZ, JA .

ORGANOMETALLICS, 1990, 9 (10) :2819-2831

[3] N-bonded enolatorhenium(I) complexes having dimethylphenylphosphine ligands as active key intermediates in catalytic Knoevenagel and Michael reactions [J].

Hirano, M ;

Hirai, M ;

Ito, Y ;

Tsurumaki, T ;

Baba, A ;

Fukuoka, A ;

Komiya, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 569 (1-2) :3-14

[4] SYNTHESIS OF NOVEL RHENIUM(I) ENOLATE COMPLEXES AS ACTIVE KEY INTERMEDIATES IN THE CATALYTIC ALDOL-TYPE REACTION [J].

HIRANO, M ;

ITO, Y ;

HIRAI, M ;

FUKUOKA, A ;

KOMIYA, S .

CHEMISTRY LETTERS, 1993, (12) :2057-2060

[5] Synthesis of N-bonded enolatoruthenium(II) by oxidative addition of alkyl cyanocarboxylate to a ruthenium(0) complex [J].

Hirano, M ;

Takenaka, A ;

Mizuho, Y ;

Hiraoka, M ;

Komiya, S .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (18) :3209-3216

[6] CHEMISTRY OF 2-NAPHTHYL BIS[BIS(DIMETHYLPHOSPHINO)ETHANE] HYDRIDE COMPLEXES OF FE, RU, AND OS .2. CLEAVAGE OF SP AND SP3 C-H, C-O, AND C-X BONDS - COUPLING OF CARBON-DIOXIDE AND ACETONITRILE [J].

ITTEL, SD ;

TOLMAN, CA ;

ENGLISH, AD ;

JESSON, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (24) :7577-7585

[7] ALKYLIRON AND ALKYLCOBALT REAGENTS .4. ALDEHYDE-SELECTIVE CYANOALKYLATION WITH CYANOALKYL DERIVATIVES OF IRON(II) AND OTHER TRANSITION-METALS [J].

KAUFFMANN, T ;

KIEPER, H ;

PIEPER, H .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (04) :899-905

[8] ZINC AND COPPER CARBENOIDS AS EFFICIENT AND SELECTIVE A1/D1 MULTICOUPLING REAGENTS .1. [J].

KNOCHEL, P ;

JEONG, N ;

ROZEMA, MJ ;

YEH, MCP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6474-6476

[9] FORMATION AND EFFICIENT ADDITION OF CERIUM(III) DERIVATIVE OF ACETONITRILE TO KETONES [J].

LIU, HJ ;

ALSAID, NH .

TETRAHEDRON LETTERS, 1991, 32 (40) :5473-5476

[10] C-H BOND ACTIVATION BY RUTHENIUM(0) COMPLEXES - ISOLATION OF AN ACTIVE INTERMEDIATE IN THE RUTHENIUM CATALYZED ALDOL AND MICHAEL REACTIONS [J].

MIZUHO, Y ;

KASUGA, N ;

KOMIYA, S .

CHEMISTRY LETTERS, 1991, (12) :2127-2130