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B–O–B Catalyzed Cycloadditions of Acrylic Acids

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Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Sustainable Chem. Eng. 2016, 4, 12, 6991-6995
    Research Article

    B–O–B Catalyzed Cycloadditions of Acrylic Acids
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    † Department of Chemistry, 578 South Shaw Lane, Michigan State University, East Lansing, Michigan 48824, United States
    ‡ The Coca-Cola Company, 1 Coca-Cola Plaza, NW, Atlanta, Georgia 30313, United States
    *E-mail: [email protected]. Phone: 517-898-9355.
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    ACS Sustainable Chemistry & Engineering

    Cite this: ACS Sustainable Chem. Eng. 2016, 4, 12, 6991–6995
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    https://doi.org/10.1021/acssuschemeng.6b01908
    Published September 28, 2016
    Copyright © 2016 American Chemical Society
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    Abstract

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    Lewis-acid-catalyzed cycloadditions of unesterified acrylic acids performed under solvent-free reaction conditions can be environmentally advantageous and afford increased product yields. However, there is also the potential for competing Lewis-acid-catalyzed polymerization reactions and the attendant fire/explosion risks associated with runaway polymerizations. BOB(OAc)4 (tetraacetyl diborate) and BOBPh4 (diphenylborinic anhydride), which are distinguished by an oxygen bonded to two boron atoms (B–O–B), catalyze high-yielding cycloadditions of unesterified acrylic acids under solvent-free reaction conditions without competing olefin polymerization.

    Copyright © 2016 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/acssuschemeng.6b01908.

    • Figure S1, BOB(OAc)4 crystallographic data, experimental procedures, and spectroscopic data (PDF)

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    Cited By

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    This article is cited by 9 publications.

    1. Yuta Chikashige, Tsunayoshi Takehara, Tsuyoshi Matsuzaki, Takeyuki Suzuki, Kenichi Murai, Mitsuhiro Arisawa, Makoto Sako. Axially Chiral Borinic Acid Catalysts: Design, Synthesis, and Application in Alkylative Desymmetrization of 1,2-Diols. The Journal of Organic Chemistry 2023, 88 (19) , 14178-14183. https://doi.org/10.1021/acs.joc.3c01143
    2. Naoyuki Shimada, Mai Hirata, Masayoshi Koshizuka, Naoki Ohse, Ryoto Kaito, Kazuishi Makino. Diboronic Acid Anhydrides as Effective Catalysts for the Hydroxy-Directed Dehydrative Amidation of Carboxylic Acids. Organic Letters 2019, 21 (11) , 4303-4308. https://doi.org/10.1021/acs.orglett.9b01484
    3. Lingli Ni, Jiayu Xin, Kun Jiang, Lu Chen, Dongxia Yan, Xingmei Lu, and Suojiang Zhang . One-Step Conversion of Biomass-Derived Furanics into Aromatics by Brønsted Acid Ionic Liquids at Room Temperature. ACS Sustainable Chemistry & Engineering 2018, 6 (2) , 2541-2551. https://doi.org/10.1021/acssuschemeng.7b04017
    4. Vadim V. Bardin, Nicolay Yu. Adonin. Preparation of arylboronic and diarylborinic acids from potassium aryl(fluoro)borates. Monatshefte für Chemie - Chemical Monthly 2024, 155 (7) , 725-730. https://doi.org/10.1007/s00706-024-03213-4
    5. Xin Zhang, Liu Leo Liu. Reactivity of a Free Aluminylene towards Boron Lewis Acids: Accessing Aluminum‐Boron‐Bonded Species. European Journal of Inorganic Chemistry 2023, 26 (25) https://doi.org/10.1002/ejic.202300157
    6. Anne‐Frédérique Pécharman, Michael S. Hill, Mary F. Mahon. Synthesis of Unsymmetrical Diboranes by Diborane Metathesis. Angewandte Chemie 2018, 130 (33) , 10848-10851. https://doi.org/10.1002/ange.201803607
    7. Anne‐Frédérique Pécharman, Michael S. Hill, Mary F. Mahon. Synthesis of Unsymmetrical Diboranes by Diborane Metathesis. Angewandte Chemie International Edition 2018, 57 (33) , 10688-10691. https://doi.org/10.1002/anie.201803607
    8. Yunwen Tao, Wenli Zou, Dieter Cremer, Elfi Kraka. Correlating the vibrational spectra of structurally related molecules: A spectroscopic measure of similarity. Journal of Computational Chemistry 2018, 39 (6) , 293-306. https://doi.org/10.1002/jcc.25109
    9. Sergey Arkhipenko, Marco T. Sabatini, Andrei S. Batsanov, Valerija Karaluka, Tom D. Sheppard, Henry S. Rzepa, Andrew Whiting. Mechanistic insights into boron-catalysed direct amidation reactions. Chemical Science 2018, 9 (4) , 1058-1072. https://doi.org/10.1039/C7SC03595K
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    ACS Sustainable Chemistry & Engineering

    Cite this: ACS Sustainable Chem. Eng. 2016, 4, 12, 6991–6995
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acssuschemeng.6b01908
    Published September 28, 2016
    Copyright © 2016 American Chemical Society
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