Nickel catalyzed enantioselective hydroarsination of nitrostyrene

Abstract

A catalytic asymmetric hydroarsination reaction of an activated alkene viz. (E)-nitrostyrene was developed using chiral PCP Pt-, Pd- and Ni-pincer complexes as catalysts. The corresponding chiral tertiary arsine adduct was obtained in ees of up to 80% under mild reaction conditions using the PCP Ni–Cl pincer catalyst. The arsine adduct was furnished with catalyst loadings of 1–5 mol% and the reaction duration ranging from <5 min to 180 min. The subsequent coordination of the hydroarsination product to gold(I) chloride allowed for the confirmation of the stereochemistry of the arsine adduct via crystallographic analysis.