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J Am Chem Soc. 2017 Sep 20;139(37):13156-13165. doi: 10.1021/jacs.7b07444. Epub 2017 Sep 11.

Base-Catalyzed Aryl-B(OH).

Journal of the American Chemical Society

Paul A Cox, Marc Reid, Andrew G Leach, Andrew D Campbell, Edward J King, Guy C Lloyd-Jones

Affiliations

  1. School of Chemistry, University of Edinburgh , Joseph Black Building, David Brewster Road, Edinburgh EH9 3FJ, U.K.
  2. School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University , Byrom Street, Liverpool L3 3AF, U.K.
  3. AstraZeneca , Silk Road Business Park, Macclesfield SK10 2NA, U.K.
  4. TgK Scientific Limited , 7 Long's Yard, St Margaret's Street, Bradford-on-Avon BA15 1DH, U.K.

PMID: 28823150 DOI: 10.1021/jacs.7b07444

Abstract

Pioneering studies by Kuivila, published more than 50 years ago, suggested ipso protonation of the boronate as the mechanism for base-catalyzed protodeboronation of arylboronic acids. However, the study was limited to UV spectrophotometric analysis under acidic conditions, and the aqueous association constants (K

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