A NEW SYNTHESIS OF SUBSTITUTED FULVENES

被引：101
作者：
LEE, GCM
TOBIAS, B
HOLMES, JM
HARCOURT, DA
GARST, ME
机构：
[1] Department of Chemical Sciences, Allergan Inc., 2525 DuPont Drive, Irvine California
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 25期
关键词：
D O I：
10.1021/ja00181a039
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new fulvene synthesis results from the palladium-catalyzed [2 + 2 + 2] annulation of 1 mol of a β-substituted vinyl iodide and 2 mol of a monosubstituted acetylene. This variant of the Heck reaction tolerates a wide range of substrate substituents with the best results obtained by using the catalyst, Pd(CH3CN)2Cl2. Addition of Cu'I to the reaction affords high yields of 1,3-enyne and no fulvene. A [6.5]spiro system is formed from 4-tert-butyl-1-cyclohexenyl triflate and a biphenyl is formed from I-aryl-1-bromoethene under these conditions. A mechanism for this novel fulvene synthesis is proposed. © 1990, American Chemical Society. All rights reserved.
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页码：9330 / 9336
页数：7
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