A Highly Regioselective Salt-Free Iron-Catalyzed Allylic Alkylation

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  • Financial support by the Fonds der Chemischen Industrie, the Deutsche Forschungsgemeinschaft, the Otto-Röhm-Gedächtnisstiftung, and the Fonds zur Förderung des wissenschaftlichen Nachwuchses im Fachbereich Chemie der Universität Dortmund is gratefully acknowledged.

Abstract

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Ironing out the kinks: A highly regioselective allylic alkylation can be performed in the presence of catalytic amounts of an iron(−II) complex and triphenylphosphane (see scheme; EWG=electron-withdrawing group). Allyl carbonates and pronucleophiles are coupled in high yields with a high regioselectivity comparable only with that obtained with Rh catalysts. The reaction is broadly applicable and does not require external base.

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