An efficient Negishi cross-coupling reaction catalyzed by nickel(II) and diethyl phosphite

被引:54
作者
Gavryushin, Andrei [1 ]
Kofink, Christiane [1 ]
Manolikakes, Georg [1 ]
Knochel, Paul [1 ]
机构
[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
关键词
D O I
10.1016/j.tet.2006.03.123
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A combination of diethyl phosphite-DMAP and Ni(II) salts forms a very effective catalytic system for the cross-coupling reactions of arylzinc halides with aryl, heteroaryl, and alkenyl bromides. chlorides. triflates. and nonaflates. The choice of solvent is quite important and the mixture of THF-N-ethylpyrrolidinone (NEP) (8: 1) was found to be optimal. The reaction usually requires only 0.05 moll % of NiCl2 or Ni(acac)(2) as catalyst and proceeds at room temperature within 1-48 h. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7521 / 7533
页数:13
相关论文
共 37 条
[1]   Modular diamino- and dioxophosphine oxides and chlorides as ligands for transition-metal-catalyzed C-C and C-N couplings with aryl chlorides [J].
Ackermann, L ;
Born, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) :2444-2447
[2]  
[Anonymous], 1998, TRANSITION METALS OR
[3]   Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides [J].
Arp, FO ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) :10482-10483
[4]   PtBr2-catalyzed consecutive enyne metathesis-aromatization of 1-(1-methoxy-but-3-enyl)-2-(1-alkynyl)benzenes:: Dual role of the Pt catalyst [J].
Bajracharya, GB ;
Nakamura, I ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (03) :892-897
[5]  
BOHM VPW, 2004, ANGEW CHEM INT EDIT, V43, P2259
[6]   PYRROLE STUDIES .27. UTILIZATION OF 1-METHYL-2-PYRROLYL LITHIUM IN THE SYNTHESIS OF 1-METHYL-2-SUBSTITUTED PYRROLES [J].
BRITTAIN, JM ;
JONES, RA ;
ARQUES, JS ;
SALIENTE, TA .
SYNTHETIC COMMUNICATIONS, 1982, 12 (03) :231-248
[7]   VINYLIC ORGANOBORANES .14. A STEREOSPECIFIC SYNTHESIS OF (E)-1-HALO-1-ALKENES FROM 1-ALKYNES [J].
BROWN, HC ;
HAMAOKA, T ;
RAVINDRAN, N ;
SUBRAHMANYAM, C ;
SOMAYAJI, V ;
BHAT, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6075-6079
[8]   New P,N Ligands for asymmetric Ir-catalyzed reactions [J].
Bunlaksananusorn, T ;
Polborn, K ;
Knochel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) :3941-3943
[9]   HIGHLY REACTIVE MAGNESIUM AND ITS APPLICATION TO ORGANIC SYNTHESES [J].
BURNS, TP ;
RIEKE, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (16) :3674-3680
[10]  
De Meijere A., 2004, Metal-Catalyzed Cross-Coupling Reactions