4.8 Article

Light-Promoted Copper-Catalyzed Enantioselective Alkylation of Azoles

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 4, Pages 2130-2134

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202009323

Keywords

alkyl bromides; asymmetric C− H functionalization; azoles; copper catalysis; enantioselectivity

Funding

  1. [NSFC-21772218]
  2. [21821002]
  3. [XDB20000000]

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A catalytic asymmetric alkylation of azoles with secondary 1-arylalkyl bromides through direct C-H functionalization was reported. The reaction, under blue-light photoexcitation, showed good reactivity and high stereoselectivity, providing an efficient strategy for the construction of chiral alkyl azoles at low temperature. The reactions are compatible with a wide range of azoles.
A catalytic asymmetric alkylation of azoles with secondary 1-arylalkyl bromides through direct C-H functionalization is reported. Under blue-light photoexcitation, a copper(I)/carbazole-based bisoxazoline (CbzBox) catalytic system exhibits good reactivity and high stereoselectivity, thus offering an efficient strategy for the construction of chiral alkyl azoles. These reactions proceed at low temperature and are compatible with a wide range of azoles.

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