Journal
CHEMICAL SCIENCE
Volume 11, Issue 12, Pages 3146-3151Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc00467g
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Funding
- NSF [1751568]
- University of Maryland College Park [CHE160082, CHE160053]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1751568] Funding Source: National Science Foundation
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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 alkyl radical intermediates out of the solvent cage to participate in an intra- or intermolecular radical cascade with a range of VCPs followed by re-entering the Fe radical cross-coupling cycle to undergo (stereo)selective C(sp(2))-C(sp(3)) bond formation. This work provides a proof-of-concept of the use of vinyl cyclopropanes as synthetically useful 1,5-synthons in Fe-catalyzed conjunctive cross-couplings with alkyl halides and aryl/vinyl Grignard reagents. 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.
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