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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.
Potter et al. (Fri,) studied this question.