ACS Publications. Most Trusted. Most Cited. Most Read
Sulfur-Directed α-C(sp3)–H Amidation of Pyrrolidines with Dioxazolones under Rhodium Catalysis

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2024, 26, 1, 57-61
    Letter

    Sulfur-Directed α-C(sp3)–H Amidation of Pyrrolidines with Dioxazolones under Rhodium Catalysis
    Click to copy article linkArticle link copied!

    Other Access OptionsSupporting Information (2)

    Organic Letters

    Cite this: Org. Lett. 2024, 26, 1, 57–61
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.3c03633
    Published December 22, 2023
    Copyright © 2023 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Site-selective functionalization of saturated N-heterocycles such as pyrrolidines is a central topic in organic synthesis and drug discovery. We herein report the sulfur-assisted rhodium(III)-catalyzed sp3 C–H amidation of pyrrolidines with dioxazolones as amidating agents. The amenability of the thioamide directing group is elucidated by a series of control experiments.

    Copyright © 2023 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.3c03633.

    • General methods, experimental procedure and characterization data of all compounds, gram-scale experiment with 1d, deuterium labeling experiment, and 1H, 13C, and 19F NMR spectra and HRMS data for all products (PDF)

    • FAIR data, including the primary NMR FID files, for compounds 1a–1f, 3aa, 3ba, 3da–3ds, 3ea, 3fa, 6a, 7a, 7b, 8a, 9b, deuterio-1d, deuterio-3da, 10a, and 10b (ZIP)

    Accession Codes

    CCDC 2289414 and 2308915 contain 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.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai
    powered by  Scite

    This article is cited by 4 publications.

    1. Shi-Hui Shi, Qing-Gen Wang, Yi-Han Yang, Xue Li, Cheng Wang, Bin Chen, Chen-Ho Tung, Li-Zhu Wu. Skeletal Reorganization of Saturated Six-Membered Aza-cycles to Sulfonated Pyrrolidines under Redox-Neutral Conditions. Organic Letters 2025, 27 (13) , 3420-3425. https://doi.org/10.1021/acs.orglett.5c00815
    2. Jeonghyun Min, Keunju Park, Kyeongwon Moon, Hyung Sik Kim, Pargat Singh, In Su Kim. Thione-Directed C–H Amidation of Chromone Analogues with Dioxazolones under Rh(III) Catalysis. Organic Letters 2024, 26 (42) , 9157-9161. https://doi.org/10.1021/acs.orglett.4c03646
    3. Tengfei Zhang, Zhe Chang, Chunxia Chen, Jinsong Peng. Progress in Functionalization of N- α -C sp 3—H Bond Catalyzed by Transition Metals. Chinese Journal of Organic Chemistry 2025, 45 (1) , 168. https://doi.org/10.6023/cjoc202404040
    4. Bosen Wang, Hao Li, Minmin Liu, Jiayi Lin, Chenglei Yang, Zhongkai Zhao, Dianjun Li, Jinhui Yang. Visible-light-induced Fe( iii )-promoted reduction amidation of 1,4,2-dioxazol-5-one. New Journal of Chemistry 2024, 48 (30) , 13654-13658. https://doi.org/10.1039/D4NJ02305F
    Download PDF
    Go to Organic Letters
    Get e-Alerts
    Get e-Alerts

    Organic Letters

    Cite this: Org. Lett. 2024, 26, 1, 57–61
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.3c03633
    Published December 22, 2023
    Copyright © 2023 American Chemical Society
    Request reuse permissions

    Article Views

    2616

    Altmetric

    -

    Citations

    4
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.