Palladium catalyzed Heck reaction of arenediazonium tetrafluoroborate salts with Baylis-Hillman adducts:: production of α-benzyl-β-keto esters

被引:64
作者
Perez, R
Veronese, D
Coelho, F
Antunes, OAC
机构
[1] Univ Fed Rio de Janeiro, Inst Quim, BR-21945970 Rio De Janeiro, Brazil
[2] Univ Estadual Campinas, Inst Quim, Dept Quim Organ, BR-13084971 Campinas, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
D O I
10.1016/j.tetlet.2005.12.058
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel experimental procedure to obtain alpha-benzyl-beta-keto esters from the Heck reaction between arenediazonium tetrafluoroborate salts and Baylis-Hillman (BH) adducts in the presence of Pd(OAc)(2) as catalyst is described. The methodology is simple, straightforward and the use of arenediazonium salts as opposed to conventional arylhalides/triflates over the usual Heck reaction is highlighted. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1325 / 1328
页数:4
相关论文
共 51 条
[1]   Reevaluation of the mechanism of the Baylis-Hillman reaction: Implications for asymmetric catalysis [J].
Aggarwal, VK ;
Fulford, SY ;
Lloyd-Jones, GC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) :1706-1708
[2]   An easy and stereoselective synthesis of N-Boc-dolaproine via the Baylis-Hillman reaction [J].
Almeida, WP ;
Coelho, F .
TETRAHEDRON LETTERS, 2003, 44 (05) :937-940
[3]   Piperonal as electrophile in the Baylis-Hillman reaction.: A synthesis of hydroxy-β-piperonyl-γ-butyrolactone derivative [J].
Almeida, WP ;
Coelho, F .
TETRAHEDRON LETTERS, 1998, 39 (47) :8609-8612
[4]   Mechanistic and kinetic studies of palladium catalytic systems [J].
Amatore, C ;
Jutand, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :254-278
[5]  
AMEER F, 1986, S AFR J CHEM, V39, P57
[6]   Heterogeneous or homogeneous? A case study involving palladium-containing perovskites in the Suzuki reaction [J].
Andrews, SP ;
Stepan, AF ;
Tanaka, H ;
Ley, SV ;
Smith, MD .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (05) :647-654
[7]   Arylation of the Baylis-Hillman adducts [J].
Basavaiah, D ;
Muthukumaran, K .
TETRAHEDRON, 1998, 54 (19) :4943-4948
[8]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
[9]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[10]   Application of a new combination of palladium and CaCO3 for an aerobic heck reaction using arenediazonium-salts [J].
Brunner, H ;
de Courcy, NLC ;
Genêt, JP .
TETRAHEDRON LETTERS, 1999, 40 (26) :4815-4818