Asst Prof WU Jie
and his research group from the Department of Chemistry, NUS have developed a visible-light-promoted Ni-catalyzed C(sp3
)-H alkenylation of ethers and amides with excellent selectivity in a green fashion. The functionalization of carbon–hydrogen (C–H) bonds is one of the most attractive strategies for molecular construction in organic synthesis, owing to its relative abundance in organic molecules and its availability for functionalization at almost any stage in a synthetic sequence. Through the synergistic combination of photoredox and Ni catalysis, the direct C(sp3
)-H alkenylation was achieved in an atom-efficient, additive-free, and ligand-free manner. An unusual regioselectivity was observed for the alkenylation, which was complementary to that of conventional radical addition processes. Mechanistic investigation indicatesd a rare example of nickel-hydride generation with C(sp3
)-H bonds as the hydride source. This work has recently been published in J. Am. Chem. Soc. (DOI: 10.1021/jacs.7b08158).