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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_? -C_? 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.

SUBMITTER: Li W

PROVIDER: S-EPMC6771714 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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

Li Wu W Liu Weiping W Leonard David K DK Rabeah Jabor J Junge Kathrin K Brückner Angelika A Beller Matthias M

Angewandte Chemie (International ed. in English) 20190701 31

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 Cα -Cβ bond scission in >70 amines with excellent functional group tolerance. This transformation establishes tertiary amines as a general ...[more]

PMID: 31125156

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