Synthesis of 2,5-Disubstituted 3-Iodofurans via Palladium-Catalyzed Coupling and Iodocyclization of Terminal Alkynes

被引：73
作者：
Chen, Zhengwang [1 ]
Huang, Gao [1 ]
Jiang, Huanfeng [1 ]
Huang, Huawen [1 ]
Pan, Xiaoyan [1 ]
机构：
[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 04期
基金：
中国国家自然科学基金;
关键词：
HIGHLY SUBSTITUTED FURANS; FUNCTIONALIZED CONJUGATED ENYNES; RING-OPENING CYCLOISOMERIZATION; ELECTRON-DEFICIENT ALKYNES; POT CYCLIZATION REACTION; C BOND FORMATION; POLYSUBSTITUTED FURANS; EFFICIENT SYNTHESIS; TETRASUBSTITUTED FURANS; DOMINO PROCESS;
D O I：
10.1021/jo1023987
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2,5-Disubstituted 3-iodofurans are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of (Z)-beta-bromoenol acetates and terminal alkynes, followed by iodocyclization. The useful intermediates conjugated enyne acetates are obtained in high yields in the transformation. Aryl- and alkyl-substituted alkynes undergo iodocyclization in good yields. The resulting iodine-containing furans can be readily elaborated to 2,3,5-trisubstituted furans.
引用
收藏
页码：1134 / 1139
页数：6
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