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Journal Article

Iron-Catalyzed Cross-Coupling of 1-Alkynylcyclopropyl Tosylates and Related Substrates

MPS-Authors
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Tindall,  Daniel J.
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

Tindall, D. J., Krause, H., & Fürstner, A. (2016). Iron-Catalyzed Cross-Coupling of 1-Alkynylcyclopropyl Tosylates and Related Substrates. Advanced Synthesis & Catalysis, 358(15), 2398-2403. doi:10.1002/adsc.201600357.


Cite as: https://hdl.handle.net/11858/00-001M-0000-002B-260B-6
Abstract
1-Alkynylcyclopropyl tosylates react with alkylmagnesium halides in the presence of catalytic ferric acetylacetonate [Fe(acac)3] under net propargylic substitution; allene formation, which is the prevalent reactivity mode of propargylic substrates otherwise, was noticed as a side reaction only when branched alkyl- or aryl-Grignard reagents were used. These transformations represent the first successful iron-catalyzed cross-coupling reactions of tert-alkyl electrophiles.