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可见光诱导的未活化烯烃通过自由基加成/休斯-斯迈尔斯重排串联反应进行的烷基芳基化反应。

Visible-Light-Induced Alkylarylation of Unactivated Alkenes via Radical Addition/Truce-Smiles Rearrangement Cascade.

作者信息

He Chonglong, Zhang Keyuan, Wang Dan-Ning, Wang Min, Niu Yuejie, Duan Xin-Hua, Liu Le

机构信息

School of Chemistry, Xi'an Key Laboratory of Sustainable Energy Material Chemistry, and MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi'an Jiaotong University, Xi'an 710049, China.

出版信息

Org Lett. 2022 Apr 15;24(14):2767-2771. doi: 10.1021/acs.orglett.2c00875. Epub 2022 Apr 4.

Abstract

We disclosed a visible-light-induced alkylarylation reaction of unactivated alkenes via a metal-free radical addition/aryl translocation cascade sequence. Distal olefinic sulfonate was designed as a unique molecular scaffold allowing for a domino process to synthesize valuable alkylarylated alcohols in good yields with excellent diastereoselectivity, featuring mild reaction conditions, broad substrate scope, and excellent functional group tolerance. The mechanism investigation suggests that a visible-light-induced radical chain process dominates the cascade transformation.

摘要

我们报道了一种通过无金属自由基加成/芳基迁移串联反应实现的未活化烯烃的可见光诱导烷基芳基化反应。远端烯基磺酸盐被设计为一种独特的分子骨架,可通过多米诺过程以良好的产率和优异的非对映选择性合成有价值的烷基芳基化醇,具有反应条件温和、底物范围广和优异的官能团耐受性等特点。机理研究表明,可见光诱导的自由基链过程主导了串联转化。

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