General and selective metal-free radical ?-C-H borylation of aliphatic amines

Despite recent developments, selective C(sp3)-H borylation of feed-stock amines remains a formidable challenge. Herein, we have developed a general, mild, and photoinduced transition-metal -and strong-base-free method for a-C(sp3)-H borylation of amines. This protocol features a regioselective 1,5-hydrogen atom transfer process to access key a-aminoalkyl radical intermediate using commercially available easy-to-install/remove iodobenzoyl radical translocating group. Remarkably, this general, efficient, and opera-tionally simple method allows activation of primary and secondary a-C-H sites of a broad range of acyclic and cyclic amines toward highly regio-and diastereo-selective syntheses of valuable a-amino-boronates. Utility of this protocol has been demonstrated by its employment in late-stage borylation of structurally complex amines and formal C-H arylation reaction of amines. Thus, it is expected that this operationally simple, general, and practical method will find broad application in organic synthesis and drug discovery.