Visible-light promoted regioselective amination and alkylation of remote C(sp3)-H bonds

Quanping Guo, Qiang Peng, Hongli Chai, Yumei Huo, Shan Wang and Zhaoqing Xu ()
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Quanping Guo: Lanzhou University
Qiang Peng: Lanzhou University
Hongli Chai: Lanzhou University
Yumei Huo: Lanzhou University
Shan Wang: Lanzhou University
Zhaoqing Xu: Lanzhou University

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: Abstract The C-N cross coupling reaction has always been a fundamental task in organic synthesis. However, the direct use of N-H group of aryl amines to generate N-centered radicals which would couple with alkyl radicals to construct C-N bonds is still rare. Here we report a visible light-promoted C-N radical cross coupling for regioselective amination of remote C(sp3)-H bonds. Under visible light irradiation, the N-H groups of aryl amines are converted to N-centered radicals, and are then trapped by alkyl radicals, which are generated from Hofmann-Löffler-Freytag (HLF) type 1,5-hydrogen atom transfer (1,5-HAT). With the same strategy, the regioselective C(sp3)-C(sp3) cross coupling is also realized by using alkyl Hantzsch esters (or nitrile) as radical alkylation reagents. Notably, the α-C(sp3)-H of tertiary amines can be directly alkylated to form the C(sp3)-C(sp3) bonds via C(sp3)-H − C(sp3)-H cross coupling through the same photoredox pathway.

Date: 2020
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DOI: 10.1038/s41467-020-15167-2

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