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

页码：1134 / 1139

页数：6

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