Rh(III)-Catalyzed Aryl and Alkenyl C–H Bond Addition to Diverse Nitroalkenes

The transition-metal-catalyzed C–H
bond addition to nitroalkenes
has been developed. Very broad nitroalkene scope was observed for
this Rh­(III)-catalyzed method, including for aliphatic, aromatic,
and β,β-disubstituted derivatives. Additionally, various
directing groups and both aromatic and alkenyl C–H bonds were
effective in this transformation. Representative nitroalkane products
were converted to dihydroisoquinolones and dihydropyridones in a single
step and in high yield by iron-mediated reduction and in situ cyclization.
Moreover, preliminary success in enantioselective Rh­(III)-catalyzed
C–H bond addition to nitroalkenes was achieved as was X-ray
structural characterization of a nitronate intermediate.