Regiodivergent Halogenation of Vinylogous Esters: One-Pot, Transition-Metal-Free Access to Differentiated Haloresorcinols

被引：32

作者：

Chen, Xiaohong ^{[1
]}

Martinez, Jenny S. ^{[1
]}

Mohr, Justin T. ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 02期

关键词：

ENANTIOSELECTIVE SYNTHESIS; ENOL ETHERS; ARYL; BROMINATION; ALKYLATION; MECHANISM; PHENOLS; REARRANGEMENT; GENERATION; DIANIONS;

D O I：

10.1021/ol503561x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an efficient method for the regiodivergent synthesis of halogenated resorcinol derivatives using readily available vinylogous esters and sulfonyl halide halogen donors. Either the 4- or 6-haloresorcinol isomer is accessible from a common precursor. In contrast to conventional oxidants for arene halogenation, mild sulfonyl halides allow broad functional group compatibility. The strategy inherently differentiates the two resorcinol oxygen atoms and enhances the potential for complex molecule synthesis.

引用

收藏

页码：378 / 381

页数：4

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