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Topic: deprotection of a phenylboronate ester  (Read 2362 times)

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Offline CsJoe

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deprotection of a phenylboronate ester
« on: November 28, 2013, 05:33:25 AM »
I have a phenylboronate ester, which was created by the reaction of phenylboronic acid with a vicinal diol. Could you please recommend me a working method for the deprotection? I would like to remove the phenylboronic acid from the molecule to get the initial diol back. I have already tried using hydrogen peroxide with more or less success. It is important, that the molecule cannot be exposed to strong acidic or basic conditions due to its sensitivity towards them. I have also tried some relatively weak acids, like acetic acid and formic acid, but without any success.
Thank you very much for your answers!

Offline Archer

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Re: deprotection of a phenylboronate ester
« Reply #1 on: November 29, 2013, 03:55:13 AM »
Taken from Protective groups in Organic Synthesis, 3rd edn, T. W. Green et al.

1,3-propanediol, acetone Adv. Cabr. Chem. Biochem 35 31-80 (1978)
2-methylpentane-2,5-diol in AcOH Synthesis 270 (1991)
Acetone & H2O (4:1) 30 mins J. Chem. Soc, Perkin Trans. 1) 1863 (1981)

Other recommendation is H2O2 EtOAc but you have already had success with this.
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