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Practical Catalytic Cleavage of C(sp 3 )−C(sp 3 ) Bonds in Amines
Author(s) -
Li Wu,
Liu Weiping,
Leonard David K.,
Rabeah Jabor,
Junge Kathrin,
Brückner Angelika,
Beller Matthias
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201903019
Subject(s) - synthon , catalysis , chemistry , bond cleavage , cleavage (geology) , molecule , homogeneous , functional group , surface modification , combinatorial chemistry , homogeneous catalysis , stereochemistry , organic chemistry , materials science , polymer , fracture (geology) , composite material , thermodynamics , physics
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 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.