Practical Catalytic Cleavage of C(sp3 )-C(sp3 ) Bonds in Amines

Abstract

The selective cleavage of thermodynamically stable C(sp³ )-C(sp³ ) 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_α -C_β 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.

Keywords: C−C cleavage; air; amines; copper; morpholines.