Palladium-catalyzed cyanation of aryl halides: Recent developments and perspectives

被引:225
作者
Sundermeier, M [1 ]
Zapf, A [1 ]
Beller, M [1 ]
机构
[1] Univ Rostock, Leibniz Inst Organ Katlayse EV, D-18055 Rostock, Germany
关键词
palladium; cyanation; benzonitriles; homogeneous catalysis;
D O I
10.1002/ejic.200300162
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The palladium-catalyzed cyanation of aryl halides is an elegant method for the preparation of benzonitriles. Since its discovery in 1973, this reaction has been the topic of several investigations. Nevertheless, the general methodology is still somewhat underdeveloped compared to other palladium-catalyzed coupling reactions. Here, we summarize important developments from 1997 until 2003 in this area. Recent contributions from our group include the development of palladium/phosphane/amine catalyst systems for the cyanation of aryl chlorides, the successful cyanation of aryl halides with acetone cyanohydrin and trimethylsilyl cyanide as cyanation reagents, and a general improvement of catalyst efficiency by using a continuous dosage of cyanide sources. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
引用
收藏
页码:3513 / 3526
页数:14
相关论文
共 139 条
[1]  
AKITA Y, 1981, SYNTHESIS-STUTTGART, P974
[2]  
Allentoff AJ, 2000, J LABELLED COMPD RAD, V43, P1075, DOI 10.1002/1099-1344(20001015)43:11<1075::AID-JLCR393>3.3.CO
[3]  
2-6
[4]   Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides [J].
Alterman, M ;
Hallberg, A .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7984-7989
[5]   Formation of palladium(0) complexes from Pd(OAc)2 and a bidentate phosphine ligand (dppp) and their reactivity in oxidative addition [J].
Amatore, C ;
Jutand, A ;
Thuilliez, A .
ORGANOMETALLICS, 2001, 20 (15) :3241-3249
[6]   Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].
Amatore, C ;
Jutand, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :314-321
[7]   Application of palladium(0)-catalyzed processes to the synthesis of oxazole-containing partial ergot alkaloids [J].
Anderson, BA ;
Becke, LM ;
Booher, RN ;
Flaugh, ME ;
Harn, NK ;
Kress, TJ ;
Varie, DL ;
Wepsiec, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) :8634-8639
[8]   Cooperative catalyst effects in palladium-mediated cyanation reactions of aryl halides and triflates [J].
Anderson, BA ;
Bell, EC ;
Ginah, FO ;
Harn, NK ;
Pagh, LM ;
Wepsiec, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8224-8228
[9]   TRANSITION METAL-MEDIATED REACTIONS USING [C-11] CYANIDE IN SYNTHESIS OF C-11 LABELED AROMATIC-COMPOUNDS [J].
ANDERSSON, Y ;
LANGSTROM, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (11) :1395-1400
[10]   Molecularly defined palladium(0) monophosphine complexes as catalysts for efficient cross-coupling of aryl chlorides and phenylboronic acid [J].
Andreu, MG ;
Zapf, A ;
Beller, M .
CHEMICAL COMMUNICATIONS, 2000, (24) :2475-2476