ACS Publications. Most Trusted. Most Cited. Most Read
Zincation of Styrylsulfonium Salts
My Activity
    Letter

    Zincation of Styrylsulfonium Salts
    Click to copy article linkArticle link copied!

    Other Access OptionsSupporting Information (1)

    Organic Letters

    Cite this: Org. Lett. 2022, 24, 40, 7446–7449
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.2c03013
    Published October 4, 2022
    Copyright © 2022 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    We report the formation of zinc reagents by the reaction of styrylsulfonium salts with zinc powder. Transition metals and other additives are not required for promoting zincation. Zincation tolerates a variety of sensitive functional groups, including esters, bromides, and boronic esters, and proceeds with complete retention of stereochemistry. This method presents a practical approach to the formation of zinc reagents that can be used in a variety of functionalizations, such as halogenation, carboxylation, and Negishi cross-couplings.

    Copyright © 2022 American Chemical Society

    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.2c03013.

    • Experimental procedures, characterization data, computational details, and NMR spectra (PDF)

    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

    This article is cited by 8 publications.

    1. Fumito Saito, Simon Euteneuer. One-Pot, Three-Component Assembly of Sulfides Using a Sulfoxide Reagent as a Sulfur Dication Equivalent. Organic Letters 2023, 25 (32) , 6057-6061. https://doi.org/10.1021/acs.orglett.3c02301
    2. Kazuhiro Higuchi, Kai Yamamoto, Shunsuke Nakamura, Haruka Naruse, Motoki Ito, Shigeo Sugiyama. Preparation of Alkyl Di(p-tolyl)sulfonium Salts and Their Application in Metal-Free C(sp3)–C(sp3) and C(sp3)–C(sp2) Bond Formations. Organic Letters 2023, 25 (20) , 3766-3771. https://doi.org/10.1021/acs.orglett.3c01233
    3. Dylan E. Holst, Céline Dorval, Casey K. Winter, Ilia A. Guzei, Zachary K. Wickens. Regiospecific Alkene Aminofunctionalization via an Electrogenerated Dielectrophile. Journal of the American Chemical Society 2023, 145 (15) , 8299-8307. https://doi.org/10.1021/jacs.3c01137
    4. Xueyao Mu, Shuai Peng, Fangyao Su, Shuting Yin, Yongguo Liu, Baoguo Sun, Hongyu Tian, Sen Liang. Hydromethylthiolation of alkynes via nucleophilic addition of dimethyl disulfide in DMSO. Journal of Molecular Structure 2025, 1321 , 140226. https://doi.org/10.1016/j.molstruc.2024.140226
    5. Sven Timmann, Zeyu Feng, Manuel Alcarazo. Recent Applications of Sulfonium Salts in Synthesis and Catalysis. Chemistry – A European Journal 2024, 30 (70) https://doi.org/10.1002/chem.202402768
    6. Jodie L. Hann, Catherine L. Lyall, Gabriele Kociok‐Köhn, Chiara Faverio, G. Dan Pantoş, Simon E. Lewis. Unusual Regio‐ and Chemoselectivity in Oxidation of Pyrroles and Indoles Enabled by a Thianthrenium Salt Intermediate. Angewandte Chemie 2024, 136 (33) https://doi.org/10.1002/ange.202405057
    7. Jodie L. Hann, Catherine L. Lyall, Gabriele Kociok‐Köhn, Chiara Faverio, G. Dan Pantoş, Simon E. Lewis. Unusual Regio‐ and Chemoselectivity in Oxidation of Pyrroles and Indoles Enabled by a Thianthrenium Salt Intermediate. Angewandte Chemie International Edition 2024, 63 (33) https://doi.org/10.1002/anie.202405057
    8. Zeyu Shao, Junqi Zhou, Ziyu Wang, Biao Liu, Liang-Hua Zou, Cheng Wang, Jian Wen. Formal allylic C(sp 3 )–H alkylation of α-alkylstyrenes by rearrangement of intermediate alkenyl sulfonium salts. Organic Chemistry Frontiers 2023, 10 (13) , 3275-3279. https://doi.org/10.1039/D3QO00459G

    Organic Letters

    Cite this: Org. Lett. 2022, 24, 40, 7446–7449
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.2c03013
    Published October 4, 2022
    Copyright © 2022 American Chemical Society

    Article Views

    2575

    Altmetric

    -

    Citations

    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.