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

2019, Li, Wu, Liu, Weiping, Leonard, David K., Rabeah, Jabor, Junge, Kathrin, Brgckner, Angelika, Beller, Matthias

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 synthon for amides and provides valuable possibilities for their scalable functionalization in, for example, natural products and bioactive molecules. © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.