Palladium(II)-catalyzed addition of arylboronic acid to nitriles

被引：105
作者：
Zhao, Baowei [1 ]
Lu, Xiyan [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 38期
关键词：
palladium; nitrile; bipyridine; nucleophilic addition; ligand;
D O I：
10.1016/j.tetlet.2006.07.074
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The addition of arylboronic acid to nitriles catalyzed by palladium(II) species in the presence of bipyridine as the ligand was developed. The use of bipyridine is crucial for changing the properties of arylpalladium species from more electrophilic to more nucleophilic making the reaction possible. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6765 / 6768
页数：4
相关论文
共 24 条
[1]  
CLUKIN DA, 2003, ACCOUNTS CHEM RES, V36, P234
[2]  
De Meijere A., 2004, Metal-Catalyzed Cross-Coupling Reactions
[3]  
Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
[4]   Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].
Hassan, J ;
Sévignon, M ;
Gozzi, C ;
Schulz, E ;
Lemaire, M .
CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469
[5]   Oxindole synthesis through intramolecular nucleophilic addition of vinylpalladiums to aryl isocyanates [J].
Kamijo, S ;
Sasaki, Y ;
Kanazawa, C ;
Schüsseler, T ;
Yamamoto, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (47) :7718-7721
[6]   Carbocycle synthesis via carbopalladation of nitriles [J].
Larock, RC ;
Tian, QP ;
Pletnev, AA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3238-3239
[7]   Pd(II)-bipyridine catalyzed conjugate addition of arylboronic acid to α,β-unsaturated carbonyl compounds [J].
Lu, XY ;
Lin, SH .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9651-9653
[8]  
Miura M, 2002, TOP CURR CHEM, V219, P211
[9]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483
[10]   pH-dependent cross-coupling reactions of water-soluble organic halides with organoboron compounds catalyzed by the organometallic aqua complex [(SCS)PdII(H2O)]+ (SCS=C6H3-2,6-(CH2SBut)2) [J].
Nakai, H ;
Ogo, S ;
Watanabe, Y .
ORGANOMETALLICS, 2002, 21 (08) :1674-1678
123