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. 2017 Jan 6;7(1):150-153.
doi: 10.1021/acscatal.6b03217. Epub 2016 Dec 2.

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

Tyler J Potter  1 , David N Kamber  1 , Brandon Q Mercado  1 , Jonathan A Ellman  1
Affiliations

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

Tyler J Potter et al. ACS Catal. .

Abstract

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.

Keywords: C-H functionalization; Rh(III) catalysis; dihydroisoquinolone; enantioselective catalysis; nitroalkene.

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Figures

Scheme 1
Scheme 1. Nitroalkenes as Versatile Electrophiles
Scheme 2
Scheme 2. Proposed Mechanism for the Transformation
Scheme 3
Scheme 3. Preparation of a Rh(III) Nitronate
See this image and copyright information in PMC

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