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1,2-Silylpyridylation Reaction of Aryl Alkenes with Silylboronate
Organic Letters ( IF 4.9 ) Pub Date : 2022-07-29 , DOI: 10.1021/acs.orglett.2c02074
Liuzhou Gao 1 , Xueting Liu 1 , Guoao Li 1 , Shengda Chen 1 , Jia Cao 1 , Guoqiang Wang 1 , Shuhua Li 1
Affiliation  

A metal-free silyl-pyridylation of alkenes using silyl boronates and B2pin2 through a pyridine-mediated B-interelement activation has been demonstrated, which provides a practical strategy for a variety of C4-silylalkylated pyridines. DFT calculations and control experiments show that the reaction proceeds through a silyl radical addition/radical–radical coupling sequence. This protocol features a broad substrate scope and excellent functional group compatibility, and thus it showcases great potential in the late-stage modification of bioactive molecules.

中文翻译:

芳基烯烃与甲硅烷基硼酸酯的1,2-甲硅烷基吡啶化反应

已经证明了使用甲硅烷基硼酸盐和 B 2 pin 2通过吡啶介导的 B 元素间活化对烯烃进行无金属甲硅烷基吡啶基化,这为各种 C 4甲硅烷基烷基化吡啶提供了实用的策略。DFT 计算和控制实验表明,反应通过甲硅烷基自由基加成/自由基-自由基偶联顺序进行。该协议具有广泛的底物范围和优异的官能团兼容性,因此在生物活性分子的后期修饰中展示了巨大的潜力。
更新日期:2022-07-29
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