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Fe-Catalyzed Conjunctive Cross-Couplings of Unactivated Alkenes with Grignard Reagents

preprint
submitted on 31.03.2020, 00:24 and posted on 31.03.2020, 12:50 by Lei Liu, Wes Lee, Cassandra R. Youshaw, Mingbin Yuan, Michael B. Geherty, Peter Y. Zavalij, Osvaldo Gutierrez
The first iron-catalyzed three-component cross-coupling of unactivated olefins with alkyl halides and Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp2-hybridized nucleophiles, alkyl halides, and unactivated olefins bearing diverse functional groups to yield the desired 1,2-alkylarylated products with high regiocontrol. Further, we demonstrate that this protocol is amenable for the synthesis of new (hetero)carbocycles including tetrahydrofurans and pyrrolidines via a three-component radical cascade cyclization/arylation that forges three new C-C bonds.

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

USA

ORCID For Submitting Author

0000-0001-8151-7519

Declaration of Conflict of Interest

no conflict of interest

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