Stereoselective Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates with alkenyl bromides

被引：142

作者：

Molander, GA ^{[1
]}

Felix, LA ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 10期

关键词：

D O I：

10.1021/jo050286w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective synthesis of conjugated dienes using air-stable potassium alkenyltrifluoroborates as coupling partners is described. The palladium-catalyzed cross-coupling reaction of potassium (E)- and (Z)-alkenyltrifluoroborates with either (E)- or (Z)-alkenyl bromides proceeds readily with moderate to excellent yields to give the corresponding (E,E)-, (E,Z)-, (Z,E)-, or (Z,Z)-conjugated dienes stereospecifically. The cross-coupling can generally be effected using 5 mol % of Pd(OAc)(2), 10 mol % of PPh3, and 3 equiv of Cs2Co3 in THF-H2O (10:1). A variety of functional groups are tolerated in both coupling partners.

引用

页码：3950 / 3956

页数：7

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