Practical Catalytic Cleavage of C(sp3)−C(sp3) Bonds in Amines. (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. Volume 131:Number 31(2019)
• Page Start: 10803
• Page End: 10807
• Publication Date: 2019-07-01
• Subjects: Amine -- C-C-Spaltung -- Kupfer -- Luft -- Morpholine; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201903019
• Languages: English
• ISSNs: 0044-8249

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 : Spalten mit Luft : C(sp 3 )‐C(sp 3 )‐Einfachbindungen in Aminen können mit Kupfer‐Katalysatoren in Gegenwart von Luft gespalten werden. Der Nutzen dieser neuartigen Methode wird anhand der Cα −Cβ ‐Bindungsspaltung in >70 Aminen mit vielfältigen funktionellen Gruppen demonstriert.