Pd(0)-catalyzed allylic alkylation/Heck coupling in domino sequence

被引：24
作者：
Poli, G
Giambastiani, G
Pacini, B
机构：
[1] Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris, France
[2] Dipartimento Chim Organ Ugo Schiff, I-50121 Florence, Italy
[3] CNR, Ctr Studio Chim Struttura Composti Eterocicl, I-50121 Florence, Italy
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 31期
关键词：
palladium and compounds; allylations; Heck reactions;
D O I：
10.1016/S0040-4039(01)00951-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new molecular queuing process has been achieved, in which a single Pd-based catalytic system promotes two unrelated, sequential catalytic cycles in chronologically distinct order. This study demonstrates also that allylic alkylations can be catalyzed by the Herrmann's phosphapalladacycle, a result that further supports the involvement of a Pd(0) species in its mechanism of action. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：5179 / 5182
页数：4
相关论文
共 31 条
[1]   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
[2]  
Beller M, 1998, EUR J INORG CHEM, P29
[3]   First efficient palladium-catalyzed Heck reactions of aryl bromides with alkyl methacrylate [J].
Beller, M ;
Riermeier, TH .
TETRAHEDRON LETTERS, 1996, 37 (36) :6535-6538
[4]   Enantioselective domino Heck-allylic amination reactions [J].
Flubacher, D ;
Helmchen, G .
TETRAHEDRON LETTERS, 1999, 40 (20) :3867-3868
[5]   INTRAMOLECULAR HECK REACTION WITH SUBSTRATES POSSESSING AN ALLYLIC ALCOHOL MOIETY [J].
GAUDIN, JM .
TETRAHEDRON LETTERS, 1991, 32 (43) :6113-6116
[6]   A new palladium-catalyzed intramolecular allylation to pyrrolidin-2-ones [J].
Giambastiani, G ;
Pacini, B ;
Porcelloni, M ;
Poli, G .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) :804-807
[7]   Palladium catalysed cascade cyclisation-anion capture, relay switches and molecular queues [J].
Grigg, R ;
Sridharan, V .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :65-87
[8]   Palladacycles: Efficient new catalysts for the Heck vinylation of aryl halides [J].
Herrmann, WA ;
Brossmer, C ;
Reisinger, CP ;
Riermeier, TH ;
Ofele, K ;
Beller, M .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (08) :1357-1364
[9]   PALLADACYCLES AS STRUCTURALLY DEFINED CATALYSTS FOR THE HECK OLEFINATION OF CHLOROARENES AND BROMOARENES [J].
HERRMANN, WA ;
BROSSMER, C ;
OFELE, K ;
REISINGER, CP ;
PRIERMEIER, T ;
BELLER, M ;
FISCHER, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17) :1844-1848
[10]   Facile catalytic coupling of aryl bromides with terminal alkynes by phospha-palladacycles [J].
Herrmann, WA ;
Reisinger, CP ;
Ofele, K ;
Brossmer, C ;
Beller, M ;
Fischer, H .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 108 (02) :51-56
1234