Phosphinoyl-functionalization of unactivated alkenes through phosphinoyl radical-triggered distal functional group migration†,Organic Chemistry Frontiers

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Phosphinoyl-functionalization of unactivated alkenes through phosphinoyl radical-triggered distal functional group migration†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2018-06-28 00:00:00 , DOI: 10.1039/c8qo00558c
Dong Chen _{1,

2,

3,

4,

5} , Zhen Wu _{1,

2,

3,

4,

5} , Yingming Yao _{1,

2,

3,

4,

5} , Chen Zhu _{1,

2,

3,

4,

5}

Affiliation

Disclosed herein is a novel and practical protocol for the radical-mediated phosphinoyl-functionalization of unactivated alkenes. The P-centered radicals are generated in the presence of TBHP under mild reaction conditions, which trigger the subsequent distal functional group migration. Both phosphine oxides and phosphonates are suitable precursors for the delivery of phosphinoyl radicals. As a result, phosphinoyl radicals along with another functional group such as heteroaryl, cyano, or imino are incorporated to alkenes concurrently. A wide range of synthetically valuable alkylphosphorus compounds are furnished in good yields.

中文翻译：

通过膦酰基自由基触发的远端官能团迁移而使未活化烯烃的膦酰基官能化†

本文公开了用于未活化的烯烃的自由基介导的膦酰基官能化的新颖且实用的方案。在TBHP存在下，在温和的反应条件下会产生P中心自由基，从而触发随后的远端官能团迁移。氧化膦和膦酸酯都是用于递送膦酰基基团的合适的前体。结果，膦酰基基团与另一官能团例如杂芳基，氰基或亚氨基同时引入到烯烃中。以高收率提供了许多合成上有价值的烷基磷化合物。

更新日期：2018-06-28

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