New Insights into the Copper-Catalyzed Alkylation of Grignard and Organolithium Reagents

被引：23

作者：

Cahiez, Gerard ^{[1
]}

Gager, Olivier ^{[1
]}

Buendia, Julien ^{[1
]}

机构：

[1] Univ Paris 13, CNRS, Dept Chem, F-93017 Bobigny, France

来源：

SYNLETT | 2010年 / 02期

关键词：

alkylations; copper; cross-coupling; Grignard reactions; organometallic reagents; VINYL ORGANOCOPPER COMPOUNDS; STEREOSPECIFIC SYNTHESIS; ORGANOMETALLIC COMPOUNDS; PHENYLLITHIUM; DERIVATIVES; CARBONATION; CHEMISTRY; ACIDS;

D O I：

10.1055/s-0029-1219222

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Until now, it was considered that the copper-catalyzed alkylation of Grignard reagents gave good yields only in the presence of ligands, such as NMP or 1-phenylpropyne. We show herein that a slow and regular addition of the Grignard reagent provides similar results. With secondary and tertiary alkyl Grignard reagents, we disclosed that the presence of benzonitrile (10 mol%), a very simple ligand, is very efficient. The copper-catalyzed alkylation of organolithium compounds was also studied.

引用

页码：299 / 303

页数：5

共 32 条

[1] REACTIONS OF ENONES WITH NEW ORGANOCUPRATES, LICU2(CH3)3,LI2CU3(CH3)5, AND LI2CU(CH3)3 [J].

ASHBY, EC ;

LIN, JJ ;

WATKINS, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (06) :1099-1102

[2] COMPOSITION OF LITHIUM METHYLCUPRATES IN ETHER SOLVENTS [J].

ASHBY, EC ;

WATKINS, JJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (16) :5312-5317

[3]

BELETSKAYA IP, 1976, RUSS CHEM REV, V45, P330

[4] NEW COPPER CHEMISTRY .14. THE GILMAN REAGENT PH2CULI AND HIGHER-ORDER PH3CULI2 - C-13 AND LI-6 NMR IN DIMETHYL SULFIDE [J].

BERTZ, SH ;

DABBAGH, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3668-3670

[5]

CAHIEZ G, 1976, SYNTHESIS-STUTTGART, P245

[6] Cu-catalyzed alkylation of Grignard reagents:: A new efficient procedure [J].

Cahiez, G ;

Chaboche, C ;

Jézéquel, M .

TETRAHEDRON, 2000, 56 (18) :2733-2737

[7] ME5CU3LI2 - A REAGENT FOR CONJUGATE METHYLATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].

CLIVE, DLJ ;

FARINA, V ;

BEAULIEU, PL .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) :2572-2582

[8] REACTIONS OF ORGANOMETALLIC COMPOUNDS .1. THE RATES OF REACTION OF PHENYLLITHIUM AND OF METHYLLITHIUM WITH NORMAL- AND TERT-BUTYL CHLORIDES [J].

CRISTOL, SJ ;

RAGSDALE, JW ;

MEEK, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (02) :810-813

[9] REACTIONS OF ORGANOMETALLIC COMPOUNDS .2. THE REACTIONS OF PHENYLLITHIUM AND OF NORMAL-BUTYLLITHIUM WITH ALPHA-METHYLALLYL AND GAMMA-METHYLALLYL CHLORIDES [J].

CRISTOL, SJ ;

OVERHULTS, WC ;

MEEK, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (02) :813-815

[10] COPPER(I) CATALYZED-REACTIONS OF ORGANOLITHIUMS AND GRIGNARD-REAGENTS [J].

ERDIK, E .

TETRAHEDRON, 1984, 40 (04) :641-657

← 1 2 3 4 →