Practical Catalytic Cleavage of C(sp3)−C(sp3) Bonds in Amines. Issue 31 (1st July 2019)

• Record Type: Journal Article
• Authors: Li, Wu; Liu, Weiping; Leonard, David K.; Rabeah, Jabor; Junge, Kathrin; Brückner, Angelika; Beller, Matthias
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 31(2019)
• Page Start: 10693
• Page End: 10697
• Publication Date: 2019-07-01
• Subjects: air -- amines -- C−C cleavage -- copper -- morpholines; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201903019
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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 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. Abstract : Cutting with air : C(sp 3 )−C(sp 3 ) single bonds in amines can be cleaved 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.