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在间歇和连续流动条件下芳基卤化物的高效无金属光化学硼化反应。

Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions.

作者信息

Chen Kai, Zhang Shuai, He Pei, Li Pengfei

机构信息

Center for Organic Chemistry , Frontier Institute of Science and Technology (FIST) , Xi'an Jiaotong University , 99 Yanxiang Road , Xi'an , Shaanxi 710054 , China . Email:

出版信息

Chem Sci. 2016 Jun 1;7(6):3676-3680. doi: 10.1039/c5sc04521e. Epub 2016 Feb 1.

Abstract

A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions and shows exceptional functional group tolerance and broad substrate scope regarding both the aryl halide and the borylating reagent. Initial mechanistic experiments indicated a photolytically generated aryl radical as the key intermediate.

摘要

发现了一种在低温水溶液中芳基碘化物和溴化物快速、化学选择性且无金属的C-B键形成反应。该反应适用于间歇和连续流动条件,并且在芳基卤化物和硼化试剂方面均表现出优异的官能团耐受性和广泛的底物范围。初步机理实验表明,光解产生的芳基自由基是关键中间体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ab2/6008923/df9f7ccd1549/c5sc04521e-s1.jpg

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