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Palladium triggered diene formation from nitro allylic compounds: a versatile entry into naphthalene derivatives

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Abstract

Nitro allylic derivatives were converted into dienes through the elimination of the nitro group under basic treatment, in the presence of a palladium catalyst. This reaction probably involves the formation of a palladium π-allyl complex followed by a base-promoted β-hydride elimination. This reaction, combined with the condensation of ketones with nitromethane and the functionalization of the resulting nitrocycloalkenes, constitutes a very powerful synthetic tool for the formation of dienes. Particular attention has been brought to the application of this methodology to the formation of 1-substituted naphthalenes from 1-tetralone.

Graphical abstract: Palladium triggered diene formation from nitro allylic compounds: a versatile entry into naphthalene derivatives

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Publication details

The article was received on 10 Aug 2018, accepted on 04 Sep 2018 and first published on 05 Sep 2018


Article type: Communication
DOI: 10.1039/C8CC06536E
Citation: Chem. Commun., 2018, Advance Article
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    Palladium triggered diene formation from nitro allylic compounds: a versatile entry into naphthalene derivatives

    M. D. Kerim, S. Jia, C. Theodorakidou, S. Prévost and L. El Kaïm, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC06536E

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