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 alkeny...

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Bibliographic Details
Published in:ACS catalysis 2017-01, Vol.7 (1), p.150-153
Main Authors: Potter, Tyler J, Kamber, David N, Mercado, Brandon Q, Ellman, Jonathan A
Format: Article
Language:English
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Summary: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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.6b03217