Aminoquinoline-directed electro/Ni dual-catalyzed C(sp2)-H alkylation with alkyl bromides

Paired electrolysis offers an attractive platform for organic synthesis of avoiding the sacrificial anode. In this work, we developed a methodology of N,N' -bidentate aminoquinoline assistant-directed electro/Ni dual-catalyzed C( sp 2 )-H alkylation with alkyl bromides under the paired electrolysis. The alkyl radicals are generated from dehalogenation of the bromoalkanes by α -aminoalkyl radical formed in situ from oxidation of tertiary amine at the anode, which have been captured by the reactive intermediates of Ni-complex formed by coordination/C( sp 2 )-H activation sequences at the cathode, and then reductive elimination to give alkylation products. This method proceeded in mild reaction conditions, avoided sacrificial anode materials, and afforded 26%-89% yields. The reaction mechanism was studied through cyclic voltammetry and controlled experiments. A method of N, N'-bidentate aminoquinoline assistant-directed electro/Ni dual-catalyzed C( sp 2 )-H alkylation with unactivated alkyl bromides in the paired electrolysis under mild conditions, tertiary amine acts as both of base and XAT reagents, avoiding a sacrificial anode.