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Boronic Acid-Catalyzed Reactions of Carboxylic Acids

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Synthesis and Application of Organoboron Compounds

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 49))

Abstract

Although boric acid (B(OH)3) and boronic acids (RB(OH)2) behave as oligomeric mixtures, these boron compounds, as well as borane, electrophilically activate carboxylic acids as a mixed anhydride under equilibrium. In particular, electron-deficient arylboronic acids are useful as Lewis or Brønsted acid catalysts. The pK a of boronic acids is in the range of 5–9, which is significantly higher than that of the strong protic acids. However, diortho-substituted arylboronic acids with electron-withdrawing groups are unstable and are easily decomposed by base-promoted protodeboronation. In this chapter, the main emphasis is upon the recent progress on boronic acid-catalyzed reactions of carboxylic acids, as well as a few other reactions which can be catalyzed by boronic acids.

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Authors and Affiliations

  1. Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8603, Japan

    Kazuaki Ishihara

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  1. Kazuaki Ishihara
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Correspondence to Kazuaki Ishihara .

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Editors and Affiliations

  1. Universitat Rovira i Virgili Directora TECAT, Tarragona, Spain

    Elena Fernández

  2. Department of Chemistry, Centre for Sustainable Chemical Processes, Durham, United Kingdom

    Andrew Whiting

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Ishihara, K. (2015). Boronic Acid-Catalyzed Reactions of Carboxylic Acids. In: Fernández, E., Whiting, A. (eds) Synthesis and Application of Organoboron Compounds. Topics in Organometallic Chemistry, vol 49. Springer, Cham. https://doi.org/10.1007/978-3-319-13054-5_8

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