Nickel-Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines

Article abstract of DOI:10.1002/anie.201707134

A nickel-catalyzed asymmetric reductive Heck reaction of aryl chlorides has been developed that affords substituted indolines with high enantioselectivity. Manganese powder is used as the terminal reductant with water as a proton source. Mechanistically, it is distinct from the palladium-catalyzed process in that the nickel–carbon bond is converted into a C?H bond to release the product through protonation instead of hydride donation followed by C?H reductive elimination on Pd.