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无需外部路易斯碱作为活化剂的可见光介导的烷基硼酸烯基化反应

Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator.

作者信息

Yue Fuyang, Dong Jianyang, Liu Yuxiu, Wang Qingmin

机构信息

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.

Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, People's Republic of China.

出版信息

Org Lett. 2021 Apr 2;23(7):2477-2481. doi: 10.1021/acs.orglett.1c00399. Epub 2021 Mar 12.

Abstract

Herein we report a protocol for the direct visible-light-mediated alkenylation of alkyl boronic acids at room temperature without an external Lewis base as an activator, and we propose a mechanism involving benzenesulfinate activation of the alkyl boronic acids. The protocol permits the efficient functionalization of a broad range of cyclic and acyclic primary and secondary alkyl boronic acids with various alkenyl sulfones. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.

摘要

在此,我们报道了一种在室温下直接通过可见光介导使烷基硼酸烯基化的方法,该方法无需外部路易斯碱作为活化剂,并且我们提出了一种涉及苯亚磺酸盐对烷基硼酸进行活化的机理。该方法允许使用各种烯基砜对多种环状和非环状伯烷基硼酸和仲烷基硼酸进行高效官能化。我们通过制备或官能化几种药物和天然产物证明了其效用。

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