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Active Species and Mechanistic Pathways in Iron-Catalyzed C-C Bond-Forming Cross-Coupling Reactions

Journal article
Authors Carlo Cassani
Giulia Bergonzini
Carl Johan Wallentin
Published in Acs Catalysis
Volume 6
Issue 3
Pages 1640-1648
ISSN 2155-5435
Publication year 2016
Published at Department of Chemistry and Molecular Biology
Pages 1640-1648
Language en
Links dx.doi.org/10.1021/acscatal.5b02441
https://gup.ub.gu.se/file/206943
Keywords iron, cross-coupling, oxidation state, Grignard reagents, reaction mechanism, aryl grignard-reagents, secondary alkyl-halides, bearing beta-hydrogens, organic halides, organomanganese reagents, carbene catalysts, alkenyl, halides, complex, kumada, fe, Chemistry, mura m,
Subject categories Chemical Sciences

Abstract

Over the past decade, considerable progress on iron-catalyzed C-C bond-forming cross-coupling reactions has been made, leading to the successful development of several new catalytic systems. This perspective presents the proposed mechanistic pathways of iron-mediated cross-coupling reactions of organohalides and Grignard reagents and discusses the evidence documented in the literature that distinguishes whether such pathways proceed via single- or double-electron processes. When cross-coupling reactions are conducted in the presence of ligands, there is still much discussion in the literature as to whether the lowest iron oxidation state responsible for catalytic activity is Fe(I) or Fe(II). However, when ligand-free conditions are employed, it has been shown that iron reaches an Fe(I) oxidation state, allowing an Fe(I)/Fe(III) catalytic cycle. Moreover, for cross-couplings using alkyl halide electrophiles, evidence suggests that the reaction proceeds through single-electron steps, with the generation of an alkyl radical. While this topic is still the subject of much debate, it is thought that reactions of alkyl Grignards with aryl and alkenyl electrophiles proceed via a double-electron pathway.

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