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DPPF-Catalyzed Atom-Transfer Radical Cyclization via Allylic Radical
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    DPPF-Catalyzed Atom-Transfer Radical Cyclization via Allylic Radical
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    Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
    School of Petrochemical Engineering, Changzhou University, 1 Gehu Road, Changzhou 213164, China
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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 23, 6328–6331
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    https://doi.org/10.1021/acs.orglett.7b03135
    Published November 13, 2017
    Copyright © 2017 American Chemical Society

    Abstract

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    A general iron-catalyzed strategy for the atom-transfer radical cyclization (ATRC) of allylic halide is reported. Critical to this strategy is the use of DPPF [1,1′-bis(diphenylphosphino)ferrocene] as catalyst, which allows for efficient generation of the allylic radical species via a single-electron transfer (SET) process. The feasibility of achieving ATRC reactions of propargyl chlorides is also demonstrated, which affords products with an exocyclic allene moiety.

    Copyright © 2017 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.7b03135.

    • General procedures, data, and NMR spectra of products, and X-ray data of compound 2a (PDF)

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    CCDC 1561108 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 23, 6328–6331
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.7b03135
    Published November 13, 2017
    Copyright © 2017 American Chemical Society

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