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

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

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.

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

Complete list of metadatas

https://hal-polytechnique.archives-ouvertes.fr/hal-02094211
Contributor : Aurélien Arnoux <>
Submitted on : Tuesday, April 9, 2019 - 3:06:52 PM
Last modification on : Wednesday, July 3, 2019 - 10:48:05 AM

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

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

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