Issue 7, 2015

Palladium-catalyzed intramolecular rearrangement of vinylidenecyclopropanes through C–C bond activation

Abstract

Vinylidenecyclopropanes bearing sulfonamide can undergo a novel intramolecular rearrangement to give the corresponding functionalized dimethylenecyclopropanes in moderate to good yields in the presence of Pd(OAc)2 in toluene upon heating through C–C bond activation based on weak coordination of the sulfonamide directing group. The reaction pathway can be changed for phenyl substituted vinylidenecyclopropane, giving another type of dimethylenecyclopropane in methanol in the presence of K2CO3 under reflux.

Graphical abstract: Palladium-catalyzed intramolecular rearrangement of vinylidenecyclopropanes through C–C bond activation

Supplementary files

Article information

Article type
Research Article
Submitted
15 Ebr. 2015
Accepted
28 Ebr. 2015
First published
29 Ebr. 2015

Org. Chem. Front., 2015,2, 792-796

Author version available

Palladium-catalyzed intramolecular rearrangement of vinylidenecyclopropanes through C–C bond activation

D. Pan, G. Chen, X. Tang and M. Shi, Org. Chem. Front., 2015, 2, 792 DOI: 10.1039/C5QO00127G

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