Issue 23, 2013
From the journal:

Dalton Transactions

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

Eisuke Watanabe,a   Chiaki Miyamoto,a   Asumi Tanaka,a   Kenzo Iizuka,a   Satoshi Iwatsuki,b   Masahiko Inamo,c   Hideo D. Takagid  and  Koji Ishihara*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Okubo, Shinjuku-ku, Tokyo 169-8555, Japan
E-mail: ishi3719@waseda.jp

b Department of Chemistry, Konan University, Higashinada-ku, Kobe 658-8501, Japan

c Department of Chemistry, Aichi University of Education, Kariya 448-8542, Japan

d Inorganic Chemistry Division, Research Center for Materials Science, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8602, Japan

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.

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

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Article information

DOI
https://doi.org/10.1039/C3DT50283J
Article type
Paper
Submitted
28 Jan 2013
Accepted
11 Mar 2013
First published
26 Apr 2013

Dalton Trans., 2013,42, 8446-8453

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

E. Watanabe, C. Miyamoto, A. Tanaka, K. Iizuka, S. Iwatsuki, M. Inamo, H. D. Takagi and K. Ishihara, Dalton Trans., 2013, 42, 8446 DOI: 10.1039/C3DT50283J

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