Merging Electron Transfer with 1,2-Metalate Rearrangement: Deoxygenative Arylation of Inert Amides with Arylboronic Esters

Amides are essentially inert carboxyl derivatives in many types of chemical transformations. In particular, deoxygenative C-C bond formation of amides to synthetically important amines is a long-standing challenge for synthetic chemists due to the inertness of the resonance-stabilized amide C=O bond. Herein, it is disclosed that by merging electron transfer induced activation with 1,2-metalate rearrangement, a wide range of inert amides react smoothly with arylboron regents, affording a series of biologically relevant diarylmethylamines as deoxygenative C-C bond cross coupling products. With its simplicity and versatility, it shows great promise in synthesis of amines from amides, which may open up new avenues in retrosynthetic planning and find widespread use in academia and industry.