Palladium-catalyzed cross-coupling of acetates of Bbaylis-Hillman adducts and potassium organotrifluoroborates

被引：93

作者：

Kabalka, GW ^{[1
]}

Venkataiah, B

Dong, G

机构：

[1] Univ Tennessee, Dept Chem, Knoxville, TN 37996 USA

[2] Univ Tennessee, Dept Radiol, Knoxville, TN 37996 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 21期

关键词：

D O I：

10.1021/ol0351798

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The cross-coupling of potassium organotrifluoroborates and acetates of Baylis-Hillman adducts proceeds readily in moderate to excellent yield in the presence of Pd(OAc)(2). The reaction tolerates hindered trifluoroborate salts, and the process is stereoselective.

引用

收藏

页码：3803 / 3805

页数：3

相关论文

共 35 条

[1]

Basavaiah D, 1996, SYNLETT, P393

[2] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].

Basavaiah, D ;

Rao, PD ;

Hyma, RS .

TETRAHEDRON, 1996, 52 (24) :8001-8062

[3] The Friedel-Crafts reaction of the Baylis-Hillman adducts [J].

Basavaiah, D ;

Krishnamacharyulu, M ;

Hyma, RS ;

Pandiaraju, S .

TETRAHEDRON LETTERS, 1997, 38 (12) :2141-2144

[4]

BASAVAIAH D, 1994, CHEM COMMUN, P1091

[5] Synthesis and cross-coupling reactions of tetra alkylammonium organotrifluoroborate salts [J].

Batey, RA ;

Quach, TD .

TETRAHEDRON LETTERS, 2001, 42 (52) :9099-9103

[6]

Bouyssi D, 2002, EUR J ORG CHEM, V2002, P2445

[7] Cross-coupling reactions of arenediazonium tetrafluoroborates with potassium aryl- or alkenyltrifluoroborates catalyzed by palladium [J].

Darses, S ;

Genet, JP ;

Brayer, JL ;

Demoute, JP .

TETRAHEDRON LETTERS, 1997, 38 (25) :4393-4396

[8] Potassium vinyltrifluoroborate:: A stable and efficient vinylating agent of arenediazonium salts using palladium catalysts [J].

Darses, S ;

Michaud, G ;

Genêt, JP .

TETRAHEDRON LETTERS, 1998, 39 (28) :5045-5048

[9] SYNTHETIC POTENTIAL OF THE TERTIARY-AMINE-CATALYSED REACTION OF ACTIVATED VINYL CARBANIONS WITH ALDEHYDES [J].

DREWES, SE ;

ROOS, GHP .

TETRAHEDRON, 1988, 44 (15) :4653-4670

[10] Preparation of substituted allyl acetates and sulfones from Baylis-Hillman adducts in ionic liquid media [J].

Kabalka, GW ;

Venkataiah, B ;

Dong, G .

TETRAHEDRON LETTERS, 2003, 44 (25) :4673-4675

← 1 2 3 4 →