ACS Publications. Most Trusted. Most Cited. Most Read

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2015, 80, 13, 6897-6902
RETURN TO ISSUEPREVNoteNEXT

Study of the Reactivity of [Hydroxy(tosyloxy)iodo]benzene Toward Enol Esters to Access α-Tosyloxy Ketones

View Author Information
Université of Sherbrooke, CCVC, Department of Chemistry, 2500 Boul. de l’Université, Sherbrooke, Québec J1K 2R1, Canada
*E-mail: [email protected]
Cite this: J. Org. Chem. 2015, 80, 13, 6897–6902
Publication Date (Web):June 22, 2015
https://doi.org/10.1021/acs.joc.5b00948
Copyright © 2015 American Chemical Society
Request reuse permissions

    Article Views

    2246

    Altmetric

    -

    Citations

    26
    LEARN ABOUT THESE METRICS
    Read OnlinePDF (494 KB)
    Get e-Alerts
    Supporting Info (1)»
    SUBJECTS:

    Abstract

    Abstract Image

    The reactivity of enol esters toward [hydroxy(tosyloxy)iodo]benzene (HTIB) was assessed. These substrates were found to be rapidly converted in high yields to their corresponding α-tosyloxy ketones. This transformation demonstrates that these substrates can act as ketone surrogates. The scope of the method was investigated and aromatic, aliphatic, and cyclic enol esters were found to be suitable substrates for the reaction. The relative reactivity of a model substrate toward HTIB and m-CPBA was investigated, and it was found that the reaction could be performed under catalytic conditions.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    NMR spectra for all new compounds. The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.5b00948.

    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

    This article is cited by 26 publications.

    1. Tommy Lussier, Claude Y. Legault. Iodine(III)-Mediated Enantioselective Oxidative Contraction of Dihydropyranones. Organic Letters 2023, 25 (16) , 2825-2829. https://doi.org/10.1021/acs.orglett.3c00759
    2. Eietsu Hasegawa, Naoki Yoshioka, Tsukasa Tanaka, Taisei Nakaminato, Kazuki Oomori, Tadaaki Ikoma, Hajime Iwamoto, Kan Wakamatsu. Sterically Regulated α-Oxygenation of α-Bromocarbonyl Compounds Promoted Using 2-Aryl-1,3-dimethylbenzimidazolines and Air. ACS Omega 2020, 5 (13) , 7651-7665. https://doi.org/10.1021/acsomega.0c00509
    3. Atul A. More, Sourav K. Santra, Alex M. Szpilman. Azido-Enolonium Species in C–C and C–N Bond-Forming Coupling Reactions. Organic Letters 2020, 22 (3) , 768-771. https://doi.org/10.1021/acs.orglett.9b03824
    4. Bowen Xu, Yiping Gao, Jianwei Han, Zejing Xing, Sihan Zhao, Ziyang Zhang, Runlin Ren, Limin Wang. Hypervalent Iodine(III)-Mediated Tosyloxylation of 4-Hydroxycoumarins. The Journal of Organic Chemistry 2019, 84 (16) , 10136-10144. https://doi.org/10.1021/acs.joc.9b01323
    5. Robin Dagenais, Tommy Lussier, Claude Y. Legault. Iodine(III)-Mediated Contraction of 3,4-Dihydropyranones: Access to Polysubstituted γ-Butyrolactones. Organic Letters 2019, 21 (13) , 5290-5294. https://doi.org/10.1021/acs.orglett.9b01893
    6. Jia-Feng Chen, Changkun Li. Enol Ester Synthesis via Cobalt-Catalyzed Regio- and Stereoselective Addition of Carboxylic Acids to Alkynes. Organic Letters 2018, 20 (21) , 6719-6724. https://doi.org/10.1021/acs.orglett.8b02824
    7. Antoine Jobin-Des Lauriers and Claude Y. Legault . Iodine(III)-Mediated Oxidative Hydrolysis of Haloalkenes: Access to α-Halo Ketones by a Release-and-Catch Mechanism. Organic Letters 2016, 18 (1) , 108-111. https://doi.org/10.1021/acs.orglett.5b03345
    8. Timothy R. Lex, Maria I. Swasy, and Daniel C. Whitehead . Relative Rate Profiles of Functionalized Iodoarene Catalysts for Iodine(III) Oxidations. The Journal of Organic Chemistry 2015, 80 (24) , 12234-12243. https://doi.org/10.1021/acs.joc.5b02129
    9. Benoit Basdevant and Claude Y. Legault . Enantioselective Iodine(III)-Mediated Synthesis of α-Tosyloxy Ketones: Breaking the Selectivity Barrier. Organic Letters 2015, 17 (19) , 4918-4921. https://doi.org/10.1021/acs.orglett.5b02501
    10. Kokila Sakthivel, Priyanka B. Kole, Ritu Mamgain, Fateh V. Singh. Iodine(III)-Based Hypervalent Iodine Electrophiles in Organic Synthesis. Current Organic Chemistry 2022, 26 (21) , 1917-1934. https://doi.org/10.2174/1385272827666230103110651
    11. Fateh V. Singh, Samata E. Shetgaonkar, Manjula Krishnan, Thomas Wirth. Progress in organocatalysis with hypervalent iodine catalysts. Chemical Society Reviews 2022, 51 (18) , 8102-8139. https://doi.org/10.1039/D2CS00206J
    12. Muhammet Uyanik, Kazuaki Ishihara. ASYMMETRIC HYPERVALENT IODINE CATALYSIS. 2022, 243-276. https://doi.org/10.1002/9781119736424.ch7
    13. Muhammet Uyanik. Catalytic Oxidative α‐Functionalization of Carbonyls. 2022, 275-298. https://doi.org/10.1002/9783527829569.ch10
    14. Victor-Emmanuel H. Kassin, Thomas Toupy, Guillaume Petit, Pauline Bianchi, Elena Salvadeo, Jean-Christophe M. Monbaliu. Metal-free hydroxylation of tertiary ketones under intensified and scalable continuous flow conditions. Journal of Flow Chemistry 2020, 10 (1) , 167-179. https://doi.org/10.1007/s41981-019-00073-6
    15. Santu Sadhukhan, Beeraiah Baire. Metal Free Synthesis of α‐Acetoxy/Hydroxymethyl Ketones from Propargylic acetates. ChemistrySelect 2019, 4 (12) , 3376-3380. https://doi.org/10.1002/slct.201900786
    16. R. Martin Romero, Kilian Muñiz. Carbon–Heteroatom Bond Formation Mediated by Hypervalent Iodine. 2018, 1-43. https://doi.org/10.1002/9780470682531.pat0948
    17. Tobias Hokamp, Leonardo Mollari, Lewis C. Wilkins, Rebecca L. Melen, Thomas Wirth. Alternative Strategies with Iodine: Fast Access to Previously Inaccessible Iodine(III) Compounds. Angewandte Chemie International Edition 2018, 57 (27) , 8306-8309. https://doi.org/10.1002/anie.201804642
    18. Tobias Hokamp, Leonardo Mollari, Lewis C. Wilkins, Rebecca L. Melen, Thomas Wirth. Alternative Strategien mit Iod: schneller Zugang zu bisher unzugänglichen Iod(III)‐Verbindungen. Angewandte Chemie 2018, 130 (27) , 8438-8442. https://doi.org/10.1002/ange.201804642
    19. Yang Zhang, Hua Tan, Chaochao Yue, Weibing Liu. (NH 4 ) 2 S 2 O 8 ‐Mediated Direct Oxysulfonyloxylation of Alkynes with Sulfonic Acids to Access α‐Sulfonyloxyketones. ChemistrySelect 2018, 3 (1) , 15-17. https://doi.org/10.1002/slct.201702566
    20. Benoit Basdevant, Audrey-Anne Guilbault, Samuel Beaulieu, Antoine Jobin-Des Lauriers, Claude Y. Legault. Iodine(III)-mediated synthesis of chiral α-substituted ketones: recent advances and mechanistic insights. Pure and Applied Chemistry 2017, 89 (6) , 781-789. https://doi.org/10.1515/pac-2016-1212
    21. Florence Malmedy, Thomas Wirth. Cyclization of Malonate Derivatives with Iodine(III) Reagents. European Journal of Organic Chemistry 2017, 2017 (4) , 786-789. https://doi.org/10.1002/ejoc.201601587
    22. Yang Zhang, Hua Tan, Weibing Liu. Synthesis of α-sulfonyloxyketones via iodobenzene diacetate (PIDA)-mediated oxysulfonyloxylation of alkynes with sulfonic acids. RSC Advances 2017, 7 (85) , 54017-54020. https://doi.org/10.1039/C7RA11875A
    23. Florence Malmedy, Thomas Wirth. Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents. Chemistry - A European Journal 2016, 22 (45) , 16072-16077. https://doi.org/10.1002/chem.201603022
    24. Antoine Jobin‐Des Lauriers, Claude Y. Legault. Enol and Ynol Surrogates: Promising Substrates for Hypervalent Iodine Chemistry. Asian Journal of Organic Chemistry 2016, 5 (9) , 1078-1099. https://doi.org/10.1002/ajoc.201600246
    25. Neha Taneja, Rama Krishna Peddinti. Iodobenzene and m-chloroperbenzoic acid mediated oxidative dearomatization of phenols. Tetrahedron Letters 2016, 57 (35) , 3958-3963. https://doi.org/10.1016/j.tetlet.2016.07.078
    26. Benoit Basdevant, Claude Y. Legault. ChemInform Abstract: Study of the Reactivity of [Hydroxy(tosyloxy)iodo]benzene Toward Enol Esters to Access α-Tosyloxy Ketones.. ChemInform 2015, 46 (45) , no-no. https://doi.org/10.1002/chin.201545044
    Download PDF

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect