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铜介导的烯基醛的磺酰基自由基引发的 5-endo-trig 环化反应:磺甲基 1H-茚的合成。

Cu-Mediated Sulfonyl Radical-Enabled 5- exo-trig Cyclization of Alkenyl Aldehydes: Access to Sulfonylmethyl 1 H-Indenes.

机构信息

CAS Key Laboratory of Receptor Research , Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences , Shanghai 201203 , China.

State Key Laboratory of Drug Research , Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences , Shanghai 201203 , China.

出版信息

J Org Chem. 2018 Apr 20;83(8):4598-4605. doi: 10.1021/acs.joc.8b00341. Epub 2018 Apr 6.

Abstract

An efficient method for the construction of sulfonylmethyl 1 H-indenes via Cu(I)-mediated sulfonyl radical-enabled 5- exo-trig cyclization of alkenyl aldehydes has been developed for the first time. Mechanistic studies indicated that a radical addition-cyclization-elimination (RACE) process might be involved. The reaction features a relatively broad substrate scope, good annulation efficiency, and varying functional group tolerance.

摘要

一种高效的合成方法被首次开发出来,通过铜(I)介导的磺酰基自由基促进的烯基醛的 5-endo-trig 环化反应来构建磺酰甲基 1H-茚。机理研究表明,可能涉及自由基加成-环化-消除(RACE)过程。该反应具有较广泛的底物范围、良好的环化效率和不同的官能团容忍度。

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