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http://hdl.handle.net/10397/95735
Title: | Thioether-directed NiH-catalyzed remote γ C(sp3 )−H hydroamidation of alkenes by 1,4,2-dioxazol-5-ones | Authors: | Du, B Ouyang, Y Chen, Q Yu, WY |
Issue Date: | Sep-2021 | Source: | Journal of the American Chemical Society, 22 Sept. 2021, v. 143, no. 37, p. 14962-14968 | Abstract: | A NiH-catalyzed thioether-directed cyclometalation strategy is developed to enable remote methylene C-H bond amidation of unactivated alkenes. Due to the preference for five-membered nickelacycle formation, the chain-walking isomerization initiated by the NiH insertion to an alkene can be terminated at the γ-methylene site remote from the alkene moiety. By employing 2,9-dibutyl-1,10-phenanthroline as the ligand and dioxazolones as the reagent, the amidation occurs at the γ-C(sp3)-H bonds to afford the amide products in up to 90% yield (>40 examples) with remarkable regioselectivity (up to 24:1 rr). | Publisher: | American Chemical Society | Journal: | Journal of the American Chemical Society | ISSN: | 0002-7863 | EISSN: | 1520-5126 | DOI: | 10.1021/jacs.1c05834 | Rights: | © 2021 American Chemical Society This document is the Accepted Manuscript version of a Published Work that appeared in final form in https://pubs.acs.org/journal/jacsat, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://dx.doi.org/10.1021/jacs.1c05834. Journal of the American Chemical Society is available at https://pubs.acs.org/journal/jacsat. |
Appears in Collections: | Journal/Magazine Article |
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Du_Thioether-Directed_NiH-Catalyzed_Remote.pdf | Pre-Published version | 1.2 MB | Adobe PDF | View/Open |
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