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TMEDA in iron-catalyzed Kumada coupling: amine adduct versus homoleptic "ate" complex formation

Bedford, Robin B., Brenner, Peter B., Carter, Emma, Cogswell, Paul M., Haddow, Mairi F., Harvey, Jeremy N., Murphy, Damien M., Nunn, Joshua and Woodall, Christopher H. 2014. TMEDA in iron-catalyzed Kumada coupling: amine adduct versus homoleptic "ate" complex formation. Angewandte Chemie International Edition 53 (7) , pp. 1804-1808. 10.1002/anie.201308395

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The reactions of iron chlorides with mesityl Grignard reagents and tetramethylethylenediamine (TMEDA) under catalytically relevant conditions tend to yield the homoleptic “ate” complex [Fe(mes)3]− (mes=mesityl) rather than adducts of the diamine, and it is this ate complex that accounts for the catalytic activity. Both [Fe(mes)3]− and the related complex [Fe(Bn)3]− (Bn=benzyl) react faster with representative electrophiles than the equivalent neutral [FeR2(TMEDA)] complexes. FeI species are observed under catalytically relevant conditions with both benzyl and smaller aryl Grignard reagents. The X-ray structures of [Fe(Bn)3]− and [Fe(Bn)4]− were determined; [Fe(Bn)4]− is the first homoleptic σ-hydrocarbyl FeIII complex that has been structurally characterized.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Additional Information: catalysis; cross-coupling; Grignard reagents; iron
Publisher: Wiley
ISSN: 1433-7851
Funders: EPSRC, Pfizer
Last Modified: 13 Jul 2022 06:57

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