4.8 Article

Visible-Light-Driven, Copper-Catalyzed Decarboxylative C(sp(3))-H Alkylation of Glycine and Peptides

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 48, Pages 15841-15846

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809400

Keywords

cross-coupling; copper; peptides; photochemistry; radicals

Funding

  1. NSFC [21432003]
  2. Fundamental Research Funds for the Central Universities [lzujbky-2017-127, lzujbky-2018-k9]

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Despite a well-developed and growing body of work in Cu catalysis, the potential of Cu to serve as a photocatalyst remains underexplored. Reported herein is the first example of visible-light-induced Cu-catalyzed decarboxylative C(sp(3))-H alkylation of glycine for preparing alpha-alkylated unnatural alpha-amino acids. It merits mentioning that the mild conditions and the good functional-group tolerance allow the modification of peptides using this method. The mechanistic studies revealed that a radical-radical coupling pathway is involved in the reaction.

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