4.7 Article

External Oxidant-Free Regioselective Cross Dehydrogenative Coupling of 2-Arylimidazoheterocycles and Azoles with H2 Evolution via Photoredox Catalysis

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 17, Pages 3220-3227

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800531

Keywords

C-N bond formation; Hydrogen evolution; C-H amination; Photoredox catalysis; Synergetic catalysis

Funding

  1. National Natural Science Foundation of China [21390402, 21520102003, 21272180]
  2. Natural Science Foundation of Hubei Province [2016CFB571]

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In this work, we achieved a site-selective amination of 2-arylimidazoheterocycles on the C3 position using photo-induced external oxidant-free strategy. The C-N bond formation with H-2 evolution was realized via the oxidative C-H/N-H coupling. This protocol may have significant implications in the late-modification of complicated drug molecules. In addition, we also used CV and DFT calculations to study the mechanism, which showed that the arene radical cation played an important role in accelerating the C-H amination process.

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