Relative kinetic reactivity of boronic acid and boronate ion towards Tiron, 2,2′-biphenol, and propylene glycol

Eisuke Watanabe, Chiaki Miyamoto, Asumi Tanaka, Kenzo Iizuka, Satoshi Iwatsuki, Masahiko Inamo, Hideo D. Takagi, Koji Ishihara

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18 Citations (Scopus)

Abstract

Reaction systems of boronic acid (RB(OH2), R = phenyl or 3-fluorophenyl) with diols and no proton ambiguity were elaborately set up, and kinetic measurements were conducted to elucidate the relative reactivities of RB(OH)2 and RB(OH)3-. In the reactions of phenylboronic and 3-fluorophenylboronic acids with propylene glycol, the reactivity order was: RB(OH)2 >> RB(OH)3 -, whereas in the reactions of 3-pyridylboronic acid with Tiron and 2,2′-biphenol, the reactivity of RB(OH)2 was comparable to that of RB(OH)3-. These results are in contrast to those that have been previously reported, and widely accepted for over thirty years, that concluded that the reactivity of RB(OH)3- is several orders of magnitude higher than that of RB(OH)2. The reactivity of Tiron with 3-pyridylboronic acid is affected by the protonation of one of its sulfonate groups.

Original languageEnglish
Pages (from-to)8446-8453
Number of pages8
JournalDalton Transactions
Volume42
Issue number23
DOIs
Publication statusPublished - 2013 Jun 21

ASJC Scopus subject areas

  • Inorganic Chemistry

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    Watanabe, E., Miyamoto, C., Tanaka, A., Iizuka, K., Iwatsuki, S., Inamo, M., Takagi, H. D., & Ishihara, K. (2013). Relative kinetic reactivity of boronic acid and boronate ion towards Tiron, 2,2′-biphenol, and propylene glycol. Dalton Transactions, 42(23), 8446-8453. https://doi.org/10.1039/c3dt50283j