General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis

A visible-light-promoted
photoredox/nickel protocol for the enantioselective
three-component carboarylation of alkenes with tertiary and secondary
alkyltrifluoroborates and aryl bromides is described. This redox-neutral
protocol allows for facile and divergent access to a wide array of
enantioenriched β-alkyl-α-arylated carbonyls, phosphonates,
and sulfones in high yields and excellent enantioselectivities from
readily available starting materials. We also report a modular and
enantioselective synthesis of flurbiprofen analogs and piragliatin
lead compound to demonstrate synthetic utility. Experimental and computational
mechanistic studies were performed to gain insights into the mechanism
and origin of chemo- and enantioselectivity.