Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization

被引:328
作者
Yue, DW [1 ]
Yao, TL [1 ]
Larock, RC [1 ]
机构
[1] Iowa State Univ Sci & Technol, Dept Chem, Ames, IA 50011 USA
关键词
D O I
10.1021/jo051299c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2,3-Disubstituted benzo[b]furans are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of various o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization with I-2, PhSeCl, or P-P2NC6H4SCl. Aryl- and vinylic-substituted alkynes undergo electrophilic cyclization in excellent yields. Biologically important furopyridines can be prepared by this approach in high yields.
引用
收藏
页码:10292 / 10296
页数:5
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