Cobalt-catalysed site-selective intra- and intermolecular dehydrogenative amination of unactivated sp3 carbons

Citations Over TimeTop 1% of 2015 papers

Abstract

Cobalt-catalysed sp(2) C-H bond functionalization has attracted considerable attention in recent years because of the low cost of cobalt complexes and interesting modes of action in the process. In comparison, much less efforts have been devoted to the sp(3) carbons. Here we report the cobalt-catalysed site-selective dehydrogenative cyclization of aliphatic amides via a C-H bond functionalization process on unactivated sp(3) carbons with the assistance of a bidentate directing group. This method provides a straightforward synthesis of monocyclic and spiro β- or γ-lactams with good to excellent stereoselectivity and functional group tolerance. In addition, a new procedure has been developed to selectively remove the directing group, which enables the synthesis of free β- or γ-lactam compounds. Furthermore, the first cobalt-catalysed intermolecular dehydrogenative amination of unactivated sp(3) carbons is also realized.

Related Papers

• → Rhodium(III)-Catalyzed Intermolecular Direct Amination of Aromatic C–H Bonds with N-Chloroamines(2011)220 cited
• → Rh-Catalyzed N–O Bond Cleavage of Anthranil: A C–H Amination Reagent for Simultaneous Incorporation of Amine and a Functional Group(2016)105 cited
• → Dual Role of Anthranils as Amination and Transient Directing Group Sources: Synthesis of 2-Acyl Acridines(2018)80 cited
• → Efficient synthesis of highly substituted pyrroles based on the tandem reactions: intermolecular amination and Pd(II)-catalyzed intramolecular hydroamidation(2008)32 cited
• → Photoinduced Arene C−H Amination with Ammonia: A Practical and Regioselective Strategy for Primary Amines(2023)6 cited