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Ligand-Dependent Mechanistic Dichotomy in Iron-Catalyzed Allylic Substitutions: σ-Allyl versus π-Allyl Mechanism

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  • We are grateful to the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie, the Studienstiftung des Deutschen Volkes (grants for K.M. and A.D.), and the Dr-Otto-Röhm-Gedächtnisstiftung for financial support of this work.

Abstract

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Iron at the crossroads: A remarkable mechanistic dichotomy in iron-catalyzed allylic substition increases not only the scope of regioselective allylic alkylation but could also herald the development of asymmetric allylic substitution (see Scheme, MTBE=methyl tert-butyl ether). Depending on the ligand used, either a σ- or a π-allyl mechanism is observed.

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