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

Manon Chaumontet, Riccardo Piccardi, Nicolas Audic, Julien Hitce, Jean-Louis Peglion, Eric Clot and Olivier Baudoin*

*Université Lyon 1, CNRS UMR5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, 43 Boulevard du 11 Novembre 1918, 69622 Villeurbanne, France, Email:

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

DOI: 10.1021/ja805598s


A combination of Pd(OAc)2 and PtBu3 as catalyst, K2CO3 as the base, and DMF as solvent allows the synthesis of benzocyclobutenes (BCB) by C-H activation of methyl groups. Various substituted BCBs were obtained under these conditions with good yields, including molecules that are hardly accessible by other methods.

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proposed mechanism

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

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

Key Words


ID: J48-Y2008-3360