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Design and Development of Fe-Catalyzed Intra- and Intermolecular Carbofunctionalization of Vinyl Cyclopropanes

preprint
submitted on 17.09.2019 and posted on 20.09.2019 by Lei Liu, Wes Lee, Mingbin Yuan, Chris Acha, Michael B. Geherty, Brandon Williams, Osvaldo Gutierrez
Design and implementation of the first (asymmetric) Fe-catalyzed intra- and intermolecular difunctionalization of vinyl cyclopropanes (VCPs) with alkyl halides and aryl Grignard reagents has been realized via a mechanistically driven approach. Mechanistic studies support the diffusion of the alkyl radical intermediates out of the solvent cage to participate in an intra- or -intermolecular radical cascade with the VCP followed by re-entering the Fe radical cross-coupling cycle to undergo selective C(sp2)-C(sp3) bond formation. Overall, we provide new design principles for Fe-mediated radical processes and underscore the potential of using combined computations and experiments to accelerate the development of challenging transformations.

Funding

CAREER: Computational and Experimental Mechanistic Approach to Iron Catalyst and Reaction Design

Directorate for Mathematical & Physical Sciences

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History

Email Address of Submitting Author

ogs@umd.edu

Institution

University of Maryland

Country

United States

ORCID For Submitting Author

0000-0001-8151-7519

Declaration of Conflict of Interest

no conflict of interest

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