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Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis

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    Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis
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    • Hannah L. D. Hayes
      Hannah L. D. Hayes
      EaStChem, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh EH9 3FJ, U.K.
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    • Ran Wei
      Ran Wei
      EaStChem, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh EH9 3FJ, U.K.
      More by Ran Wei
    • Michele Assante
      Michele Assante
      School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Byrom Street, Liverpool L3 3AF, U.K.
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    • Katherine J. Geogheghan
      Katherine J. Geogheghan
      EaStChem, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh EH9 3FJ, U.K.
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    • Na Jin
      Na Jin
      EaStChem, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh EH9 3FJ, U.K.
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    • Simone Tomasi
      Simone Tomasi
      Chemical Development, Pharmaceutical Technology and Development, Operations, AstraZeneca, Macclesfield SK10 2NA, U.K.
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      Orcidhttps://orcid.org/0000-0002-9373-7639
    • Gary Noonan
      Gary Noonan
      Chemical Development, Pharmaceutical Technology and Development, Operations, AstraZeneca, Macclesfield SK10 2NA, U.K.
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    • Andrew G. Leach
      Andrew G. Leach
      School of Health Sciences, Stopford Building, The University of Manchester, Oxford Road, Manchester M13 9PT, U.K.
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      Orcidhttps://orcid.org/0000-0003-1325-8273
    • Guy C. Lloyd-Jones*
      Guy C. Lloyd-Jones
      EaStChem, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh EH9 3FJ, U.K.
      *[email protected]
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      Orcidhttps://orcid.org/0000-0003-2128-6864
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    Cite this: J. Am. Chem. Soc. 2021, 143, 36, 14814–14826
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    https://doi.org/10.1021/jacs.1c06863
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    The kinetics and mechanism of the base-catalyzed hydrolysis (ArB(OR)2 → ArB(OH)2) and protodeboronation (ArB(OR)2 → ArH) of a series of boronic esters, encompassing eight different polyols and 10 polyfluoroaryl and heteroaryl moieties, have been investigated by in situ and stopped-flow NMR spectroscopy (19F, 1H, and 11B), pH-rate dependence, isotope entrainment, 2H KIEs, and KS-DFT computations. The study reveals the phenomenological stability of boronic esters under basic aqueous–organic conditions to be highly nuanced. In contrast to common assumption, esterification does not necessarily impart greater stability compared to the corresponding boronic acid. Moreover, hydrolysis of the ester to the boronic acid can be a dominant component of the overall protodeboronation process, augmented by self-, auto-, and oxidative (phenolic) catalysis when the pH is close to the pKa of the boronic acid/ester.

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    Cite this: J. Am. Chem. Soc. 2021, 143, 36, 14814–14826
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.1c06863
    Published August 30, 2021
    Copyright © 2021 American Chemical Society
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