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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(sp<sup>3</sup> )-C(sp<sup>3</sup> ) 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(sp<sup>3</sup> )-C(sp<sup>3</sup> ) 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<sub>α</sub> -C<sub>β</sub> bond scission in >70 amines with excellent functional group tolerance. This transformation establishes tertiary amines as a general  ...[more]

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