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On the Radical Nature of Iron-Catalyzed Cross-Coupling Reactions

Journal article
Authors Anna Hedström
Z. Izakian
Irma Vreto
Carl Johan Wallentin
Per-Ola Norrby
Published in Chemistry-a European Journal
Volume 21
Issue 15
Pages 5946-5953
ISSN 0947-6539
Publication year 2015
Published at Department of Chemistry and Molecular Biology
Pages 5946-5953
Language en
Links dx.doi.org/10.1002/chem.201406096
Keywords atom transfer, cross-coupling, Grignard reaction, iron, radical reactions, ARYL GRIGNARD-REAGENTS, IRON(III) AMINE-BIS(PHENOLATE) COMPLEXES, CONTINUUM DIELECTRIC THEORY, SECONDARY ALKYL-HALIDES, BEARING, BETA-HYDROGENS, H BOND ACTIVATION, ORGANIC HALIDES, ORGANOMANGANESE, REAGENTS, ELECTRONIC-STRUCTURE, HETEROARYL HALIDES, Chemistry, Multidisciplinary, MURA M, 1971, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, V93, P1487, MAO K, 1972, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, V94, P4374, NNOR DJ, 1994, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, V116, P11875, UBE H, 1953, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, V75, P4118, MURA M, 1971, SYNTHESIS-INTERNATIONAL JOURNAL OF METHODS IN SYNTHETIC ORGANIC, EMISTRY, P303
Subject categories Chemical Sciences

Abstract

The radical nature of iron-catalyzed cross-coupling between Grignard reagents and alkyl halides has been studied by using a combination of competitive kinetic experiments and DFT calculations. In contrast to the corresponding coupling with aryl halides, which commences through a classical two-electron oxidative addition/reductive elimination sequence, the presented data suggest that alkyl halides react through an atom-transfer-initiated radical pathway. Furthermore, a general iodine-based quenching methodology was developed to enable the determination of highly accurate concentrations of Grignard reagents, a capability that facilitates and increases the information output of kinetic investigations based on these substrates.

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