Direct C(sp(3))-N Radical Coupling: Photocatalytic C-H Functionalization by Unconventional Intermolecular Hydrogen Atom Transfer to Aryl Radical

  • Kang, Jihee; 
  • Hwang, Ho Seong; 
  • Soni, Vineet Kumar; 
  • Cho, Eun Jin
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초록

An unconventional approach for intermolecular direct C(sp(3))-N radical coupling has been developed by photocatalytic C(sp(3))-H activation of simple alkyl substrates using O-benzoyl oximes. The selective photocatalytic energytransfer-driven homolysis followed by decarboxylation generates the persistent iminyl radical and aryl radical, which would undergo an unprecedented intermolecular hydrogen atom abstraction from the alkyl substrate to provide the key C(sp(3)) radical. Selective radical-radical C-N cross-coupling furnishes imines which are valuable amine building blocks.

키워드

BOND FUNCTIONALIZATION; ACTIVATION; OXIDATION; ENERGIES; ETHERS; ALKYL
제목
Direct C(sp(3))-N Radical Coupling: Photocatalytic C-H Functionalization by Unconventional Intermolecular Hydrogen Atom Transfer to Aryl Radical
저자
Kang, Jihee; Hwang, Ho Seong; Soni, Vineet Kumar; Cho, Eun Jin
DOI
10.1021/acs.orglett.0c02179
발행일
2020-08-07
유형
Article
저널명
Organic Letters
권
22
호
15
페이지
6112 ~ 6116