{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Liu L"],"funding":["University of Maryland","National Science Foundation"],"pagination":["3146-3151"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8157325"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["11(12)"],"pubmed_abstract":["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 <i>via</i> 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<sup>2</sup>)-C(sp<sup>3</sup>) 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."],"journal":["Chemical science"],"pubmed_title":["Intra- and intermolecular Fe-catalyzed dicarbofunctionalization of vinyl cyclopropanes."],"pmcid":["PMC8157325"],"funding_grant_id":["1751568"],"pubmed_authors":["Acha C","Liu L","Gutierrez O","Geherty MB","Yuan M","Lee W","Williams B"],"additional_accession":[]},"is_claimable":false,"name":"Intra- and intermolecular Fe-catalyzed dicarbofunctionalization of vinyl cyclopropanes.","description":"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 <i>via</i> 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<sup>2</sup>)-C(sp<sup>3</sup>) 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.","dates":{"release":"2020-01-01T00:00:00Z","publication":"2020 Feb","modification":"2026-05-07T17:05:20.939Z","creation":"2022-02-10T14:45:43.001Z"},"accession":"S-EPMC8157325","cross_references":{"pubmed":["34122819"],"doi":["10.1039/d0sc00467g"]}}