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Direct Synthesis of Cyclopropanes from gem-Dialkyl Groups through Double C-H Activation

Antonin Clemenceau, Pierre Thesmar, Maxime Gicquel, Alexandre Le Flohic and Olivier Baudoin*

*Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland, Email:

A. Clemenceau, P. Thesmar, M. Gicquel, A. Le Flohic, O. Baudoin, J. Am. Chem. Soc., 2020, 142, 15355-15361.

DOI: 10.1021/jacs.0c05887

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An intramolecular coupling of two C-H bonds on gem-dialkyl groups is accessible using aryl bromide or triflate precursors and the 1,4-Pd shift mechanism. The use of pivalate as the base was found to be crucial to divert the mechanistic pathway toward the cyclopropane instead of the previously obtained benzocyclobutene product.

see article for more examples

Synthesis of Benzocyclobutenes by Palladium-Catalyzed C-H Activation of Methyl Groups: Method and Mechanistic Study

M. Chaumontet, R. Piccardi, N. Audic, J. Hitce, J.-L. Peglion, E. Clot, O. Baudoin, J. Am. Chem. Soc., 2008, 130, 15157-15166.

Key Words


ID: J48-Y2020