Vinylcyclopropanes as All-Carbon 1,5-Dipoles: A Reactivity Switch for Palladium-Catalyzed (5 + 4) Cycloadditions.

Org Lett

Laboratoire de Synthèse Organique, UMR 7652, Ecole Polytechnique, ENSTA ParisTech, CNRS, Palaiseau 91128 Cedex, France.

Published: March 2021

Azonanes were prepared by a palladium-catalyzed (5 + 4) cycloaddition between activated vinylcyclopropanes and 1-azadienes. During this process, the vinylcyclopropane partner displayed an unusual reactivity and behaved as an all-carbon 1,5-dipole. A ,-bidentate ligand was required to inhibit the formation of thermodynamic (3 + 2) cycloadducts.

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Source
http://dx.doi.org/10.1021/acs.orglett.1c00477DOI Listing

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