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烯丙基C(sp) -H烷基化:协同有机和光氧化还原催化的亚胺自由基加成反应

Allylic C(sp)-H alkylation synergistic organo- and photoredox catalyzed radical addition to imines.

作者信息

Jia Jiaqi, Kancherla Rajesh, Rueping Magnus, Huang Long

机构信息

Institute of Organic Chemistry, RWTH Aachen University Landoltweg 1 D-52074 Aachen Germany

KAUST Catalysis Center, KCC, King Abdullah University of Science and Technology, KAUST Thuwal 23955-6900 Saudi Arabia.

出版信息

Chem Sci. 2020 Apr 30;11(19):4954-4959. doi: 10.1039/d0sc00819b.

Abstract

A new catalytic method for the direct alkylation of allylic C(sp)-H bonds from unactivated alkenes synergistic organo- and photoredox catalysis is described. The transformation achieves an efficient, redox-neutral synthesis of homoallylamines with broad functional group tolerance, under very mild reaction conditions. Mechanistic investigations indicate that the reaction proceeds through the -centered radical intermediate which is generated by the allylic radical addition to the imine.

摘要

本文描述了一种用于从未活化烯烃直接烯丙基C(sp)-H键烷基化的新催化方法——协同有机和光氧化还原催化。该转化反应在非常温和的反应条件下,实现了具有广泛官能团耐受性的高烯丙基胺的高效、氧化还原中性合成。机理研究表明,反应通过烯丙基自由基加成到亚胺上产生的以-为中心的自由基中间体进行。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f1/8159244/014d7266c537/d0sc00819b-s1.jpg

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