Nickel-Catalyzed Directed Benzylation Of Ortho C-H Bonds In Aromatic Amides Through C-H/C-N Cleavage

Amines which are widely found in natural products,medicine,pesticides and organic synthesis intermediates play an important role in organic chemistry.In the past few decades,the discovery of effective strategies to achieve the selective C-H bond functionalizations have attracted wide attention.In contrast with the traditional coupling reactions,the direct functionalization of C–H bonds represents a powerful strategy for the synthesis of complexorganic compounds due to its high atom economy.In recent years,remarkable progress has been made in the conversion of C-H bond functionalizations catalyzed by noble metals such as palladium,rhodium and iridium.However,its applications have been limited to some extent due to the high cost of the catalyst and a certain toxicity of metal residues.Therefore,the use of inexpensive metal such as nickel,copper and iron,which are rich in reserves,low toxicity and low price to realize the inert C-H bond activations has become more and more popular among chemists.In recent years,the application of ligand-oriented strategy has greatly promoted the development of C-H bond functionalizations,the heteroatoms of the directing group coordinate with transition metals,so as to realize the selectively C-H bond functionalizations finally.On the basis of previous researchs,in this paper,we developed an efficient nickel(?)catalyzed aromatic amides ortho C-H bond benzylated reaction.By introducing 8-aminoquinoline as a directing group to realize the amide ortho C-H bond transformations and build new C-C bonds using benzylic trimethyl quaternary ammonium salts which are stable and easy made as the benzylated reagent.