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)

1 DCSO - Laboratoire de synthèse organique
2 ENSTA Paris - École Nationale Supérieure de Techniques Avancées

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.

Domaines: Chimie organique

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, 2018, 54 (77), pp.10917-10920. ⟨10.1039/c8cc06536e⟩. ⟨hal-02094211⟩