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Selective Iron-Catalyzed Cross-Coupling Reactions of Grignard Reagents with Enol Triflates, Acid Chlorides, and Dichloroarenes

MPS-Authors
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Scheiper,  Bodo
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Bonnekessel,  Melanie
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Krause,  Helga
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Scheiper, B., Bonnekessel, M., Krause, H., & Fürstner, A. (2004). Selective Iron-Catalyzed Cross-Coupling Reactions of Grignard Reagents with Enol Triflates, Acid Chlorides, and Dichloroarenes. The Journal of Organic Chemistry, 69(11), 3943-3949. doi:10.1021/jo0498866.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-9719-6
Abstract
Cheap, readily available, air stable, nontoxic, and environmentally benign iron salts such as Fe(acac)3 are excellent precatalysts for the cross-coupling of Grignard reagents with alkenyl triflates and acid chlorides. Moreover, it is shown that dichloroarene and -heteroarene derivatives as the substrates can be selectively monoalkylated by this method. All cross-coupling reactions proceed very rapidly under notably mild conditions and turned out to be compatible with a variety of functional groups in both reaction partners. A detailed analysis of the preparative results suggests that iron-catalyzed C−C bond formations can occur via different pathways. Thus, it is likely that reactions of methylmagnesium halides involve iron−ate complexes as the active components, whereas reactions of Grignard reagents with two or more carbon atoms are effected by highly reduced iron-clusters of the formal composition [Fe(MgX)2]n generated in situ. Control experiments using the ate-complex [Me4Fe]Li2 corroborate this interpretation.