Dual C(sp3)−H Bond Functionalization of N‐Heterocycles through Sequential Visible‐Light Photocatalyzed Dehydrogenation/[2+2] Cycloaddition Reactions,Angewandte Chemie International Edition

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Dual C(sp3)−H Bond Functionalization of N‐Heterocycles through Sequential Visible‐Light Photocatalyzed Dehydrogenation/[2+2] Cycloaddition Reactions
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-03-23 , DOI: 10.1002/anie.201710523
Guo-Qiang Xu _{1,

2} , Ji-Tao Xu ₁ , Zhi-Tao Feng ₁ , Hui Liang ₁ , Zhu-Yin Wang ₁ , Yong Qin ₂ , Peng-Fei Xu ₁

Affiliation

Herein we describe a mild method for the dual C(sp³)−H bond functionalization of saturated nitrogen‐containing heterocycles through a sequential visible‐light photocatalyzed dehydrogenation/[2+2] cycloaddition procedure. As a complementary approach to the well‐established use of iminium ion and α‐amino radical intermediates, the elusive cyclic enamine intermediates were effectively generated by photoredox catalysis under mild conditions and efficiently captured by acetylene esters to form a wide array of bicyclic amino acid derivatives, thus enabling the simultaneous functionalization of two vicinal C(sp³)−H bonds.

中文翻译：

N-杂环通过连续可见光光催化脱氢/ [2 + 2]环加成反应的双C（sp3）-H键官能化

在这里，我们描述了一种温和的方法，用于通过顺序可见光光催化脱氢/ [2 + 2]环加成程序对饱和含氮杂环进行双C（sp ³）-H键官能化。作为完善使用亚胺离子和α-氨基自由基中间体的一种补充方法，难以捉摸的环状烯胺中间体是在温和条件下通过光催化氧化有效产生的，并被乙炔酯有效捕获，从而形成多种双环氨基酸衍生物，从而使两个邻位C（sp ³）-H键同时功能化。

更新日期：2018-03-23

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