Remote C(sp3)–H vinylation via radical-mediated consecutive fission of C–H and C–C bonds,Organic Chemistry Frontiers

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Remote C(sp3)–H vinylation via radical-mediated consecutive fission of C–H and C–C bonds
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-09-02 , DOI: 10.1039/d0qo00952k
Tao Niu _{1,

2,

3,

4,

5} , Shan Yang _{1,

2,

3,

4,

5} , Xinxin Wu _{1,

2,

3,

4,

5} , Chen Zhu _{1,

2,

3,

4,

5}

Affiliation

Described herein is a radical-mediated vinylation of the remote C(sp³)–H bonds of propargylic alcohols. A variety of widely available reagents, such as acetonitrile, ethers, aliphatic alcohols, and simple alkanes, serve as both the solvent and coupling partner. The transformation proceeds via sequential vinyl radical-mediated HAT and intramolecular vinyl migration, in which two inert C(sp³)–H bonds and one C–C bond are homolysed. The reaction also features broad functional group tolerance, good regio-/chemo-selectivity, and synthetic step-economy.

中文翻译：

通过自由基介导的C–H和C–C键的连续裂变实现远程C（sp3）–H乙烯基化

本文描述的是炔丙醇的远端C（sp ³）-H键的自由基介导的乙烯基化。多种广泛使用的试剂，例如乙腈，醚，脂族醇和简单的烷烃，既可以作为溶剂，也可以作为偶联剂。转化过程是通过顺序的乙烯基自由基介导的HAT和分子内的乙烯基迁移进行的，其中两个惰性C（sp ³）-H键和一个C-C键被均化。该反应还具有宽泛的官能团耐受性，良好的区域/化学选择性和合成步骤经济性。

更新日期：2020-09-30

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