Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 31, Pages 10693-10697Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201903019
Keywords
air; amines; C-C cleavage; copper; morpholines
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The selective cleavage of thermodynamically stable C(sp(3))-C(sp(3)) single bonds is rare compared to their ubiquitous formation. Herein, we describe a general methodology for such transformations using homogeneous copper-based catalysts in the presence of air. The utility of this novel methodology is demonstrated for C-alpha-C-beta bond scission in >70 amines with excellent functional group tolerance. This transformation establishes tertiary amines as a general synthon for amides and provides valuable possibilities for their scalable functionalization in, for example, natural products and bioactive molecules.
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