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
[21]   Synthesis of 4-aryl-2-pyrrolidones and β-aryl-γ-amino-butyric acid (GABA) analogues by heck arylation of 3-pyrrolines with arenediazonium tetrafluoroborates.: Synthesis of (±)-rolipram on a multigram scale and chromatographic resolution by semipreparative chiral simulated moving bed chromatography [J].
Garcia, ALL ;
Carpes, MJS ;
de Oca, ACBM ;
dos Santos, MAG ;
Santana, CC ;
Correia, CRD .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (03) :1050-1053
[22]   Synthesis of 3,4-disubstituted 2,5-dihydrofurans starting from the Baylis-Hillman adducts via consecutive radical cyclization, halolactonization, and decarboxylation strategy [J].
Gowrisankar, S ;
Lee, KY ;
Kim, JN .
TETRAHEDRON LETTERS, 2005, 46 (29) :4859-4863
[23]   Synthesis of α-substituted N-aryl acrylamide derivatives through Baylis-Hillman reaction [J].
Guo, W ;
Wu, WW ;
Fan, NJ ;
Wu, ZG ;
Xia, CZ .
SYNTHETIC COMMUNICATIONS, 2005, 35 (09) :1239-1251
[26]   An enantio- and stereocontrolled synthesis of (-)-mycestericin E via cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction [J].
Iwabuchi, Y ;
Furukawa, M ;
Esumi, T ;
Hatakeyama, S .
CHEMICAL COMMUNICATIONS, 2001, (19) :2030-2031
[27]   An enantio- and stereocontrolled route to epopromycin B via cinchona alkaloid-catalyzed Baylis-Hillman reaction [J].
Iwabuchi, Y ;
Sugihara, T ;
Esumi, T ;
Hatakeyama, S .
TETRAHEDRON LETTERS, 2001, 42 (44) :7867-7871
[28]   Investigation of Pd leaching from supported Pd catalysts during the heck reaction [J].
Ji, YY ;
Jain, S ;
Davis, RJ .
JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (36) :17232-17238
[29]   Palladium-catalyzed cross-coupling of acetates of Bbaylis-Hillman adducts and potassium organotrifluoroborates [J].
Kabalka, GW ;
Venkataiah, B ;
Dong, G .
ORGANIC LETTERS, 2003, 5 (21) :3803-3805
[30]   What makes for a good catalytic cycle? A theoretical study of the role of an anionic palladium(0) complex in the cross-coupling of an aryl halide with an anionic nucleophile [J].
Kozuch, S ;
Amatore, C ;
Jutand, A ;
Shaik, S .
ORGANOMETALLICS, 2005, 24 (10) :2319-2330