Synthesis of 2-alkylidenecyclopentanones via palladium-catalyzed cross-coupling of 1-(1-alkynyl)cyclobutanols and aryl or vinylic halides

被引：56

作者：

Larock, RC ^{[1
]}

Reddy, CK ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 21期

关键词：

D O I：

10.1021/ol000219i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The palladium-catalyzed cross-coupling of aryl or vinylic halides and 1-(1-alkynyl)cyclobutanols affords good yields of stereoisomerically pure 5-arylidene- or 2-(2-alkenylidene)cyclopentanones, respectively, by a process involving (1) oxidative addition of the organic iodide to Pd(0), (2) carbopalladation of the triple bond of the 1-(1-alkynyl)cyclobutanol, (3) regio- and stereoselective ring expansion to form a novel palladiacycle, and (4) reductive elimination to the 2-alkylidenecyclopentanone with simultaneous regeneration of the Pd(0) catalyst.

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页码：3325 / 3327

页数：3

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