Iron-catalyzed allylic arylation of olefins via C(sp3)-H activation under mild conditions.

Org Lett

Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Tokyo 113-0033.

Published: February 2013

An aryl Grignard reagent in the presence of mesityl iodide converts an allylic C-H bond of a cycloalkene or an allylbenzene derivative into a C-C bond in the presence of a catalytic amount of Fe(acac)(3) and a diphosphine ligand at 0 °C. The stereo- and regioselectivity of the reaction, together with deuterium labeling experiments, suggest that C-H bond activation is the slow step in the catalytic cycle preceding the formation of an allyliron intermediate.

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http://dx.doi.org/10.1021/ol400056zDOI Listing

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