Cu(II)-Catalyzed C–N, C–O, C–Cl, C–S, and C–Se Bond Formation via C(sp2)–H Activation Using 7-Azaindole as an Intrinsic Directing Group

A general protocol has been developed for the construction of carbon-heteroatom (C-N, C-Cl, C-O, C-S, and C-Se) bonds using the bench stable, earth-abundant, and environmentally benign copper catalyst. Only oxygen is sufficient to regenerate the copper catalyst. Control experiments suggested that the proto-demetalation step is reversible. Depending on the coupling partner, the reaction follows either disproportionation or radical pathways to complete the catalytic cycle. The synthetic utility of the developed protocol has been demonstrated via various functional group transformations.