Diels-Alder reactions of hexafluoro-2-butyne with 2-heterosubstituted furans: A facile and general synthesis of 1,4-disubstituted 2,3-di(trifluoromethyl)benzenes

被引：24

作者：

Zhu, GD ^{[1
]}

Staeger, MA ^{[1
]}

Boyd, SA ^{[1
]}

机构：

[1] Abbott Labs, Div Pharmaceut Prod, Metab Dis Res, Abbott Pk, IL 60064 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 21期

关键词：

D O I：

10.1021/ol0064359

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An electron-donating heteroatom substituent at position-2 of a furan promotes regiospecific opening of the 7-oxa bridge of the Diets-Alder cycloadduct with hexafluoro-2-butyne, producing a 4-heterosubstituted 2,3-di(trifluoromethyl)phenol building block in a single step. The phenol and heteroatom substituent are easily transformed to the corresponding iodide or triflate that readily undergoes Heck, Suzuki, and Stille reactions to install a variety of substituents in high yields. This methodology provides a facile and general synthesis of 1,4-disubsituted 2,3-di(trifluoromethyl)benzenes.

引用

页码：3345 / 3348

页数：4

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