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

Mansour Dolé Kerim 1 Shuanglong Jia 1 Chrysoula Theodorakidou 1 Sébastien Prevost 1, * Laurent El Kaim 2, 1, *
* Corresponding author
1 DCSO - Laboratoire de synthèse organique
2 ENSTA Paris - École Nationale Supérieure de Techniques Avancées
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.
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Submitted on : Tuesday, April 9, 2019 - 3:06:52 PM
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Mansour Dolé Kerim, Shuanglong Jia, Chrysoula Theodorakidou, Sébastien Prevost, Laurent El Kaim. Palladium triggered diene formation from nitro allylic compounds: a versatile entry into naphthalene derivatives. Chemical Communications, Royal Society of Chemistry, 2018, 54 (77), pp.10917-10920. ⟨10.1039/c8cc06536e⟩. ⟨hal-02094211⟩

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