Helv. Chim. Acta 2021, 104, e2100102
[6] A. Mahanta, P. Adhikari, U. Bora, A. J. Thakur, ‘Biosilica as
General Procedure
an efficient heterogeneous catalyst for ipso-hydroxylation
of arylboronic acids’, Tetrahedron Lett. 2015, 56, 1780–
Arylboronic acid (0.5 mmol), Bu NBH (0.5 mmol), and
4
4
1
783.
MeCN (2 mL) were placed in a Pyrex test tube and the
mixture was irradiated by blacklight (15 W) with
stirring for 4 h (or 20 h) under an atmosphere of
oxygen. The reaction was quenched carefully using an
aqueous solution of HCl (1 N, 5 mL), and the resultant
mixture was extracted with ether (3×10 mL). The
combined organic layers were washed with brine
[
7] P. Gogoi, P. Bezboruah, J. Gogoi, R. C. Boruah, ‘ipso-
Hydroxylation of Arylboronic Acids and Boronate Esters by
Using Sodium Chlorite as an Oxidant in Water’, Eur. J. Org.
Chem. 2013, 7291–7294.
[
8] C. Zhu, R. Wang, J. R. Falck, ‘Mild and Rapid Hydroxylation
of Aryl/Heteroaryl Boronic Acids and Boronate Esters with
N-Oxides’, Org. Lett. 2012, 14, 3494–3497.
[
9] E. Kianmehr, M. Yahyaee, K. Tabatabai, ‘A mild conversion
of arylboronic acids and their pinacolyl boronate esters
into phenols using hydroxylamine’, Tetrahedron Lett. 2007,
48, 2713–2715.
(
10 mL) and dried over MgSO . After removal of the
4
solvent in a vacuum, the residue was purified through
flash column chromatography on silica gel (hexane/
ether) to give the desired hydroxyarenes.
[10] P. Lühring, A. Schumpe, ‘Gas solubilities (hydrogen, helium,
nitrogen, carbon monoxide, oxygen, argon, carbon diox-
ide) in organic liquids at 293.2 K’, J. Chem. Eng. Data 1989,
3
4, 250–252.
[
[
[
[
11] J. Xu, X. Wang, C. Shao, D. Su, G. Cheng, Y. Hu, ‘Highly
Efficient Synthesis of Phenols by Copper-Catalyzed Oxida-
tive Hydroxylation of Arylboronic Acids at Room Temper-
ature in Water’, Org. Lett. 2010, 12, 1964–1967.
Acknowledgements
I. R. thanks JSPS for a Grant-in-Aid for Scientific
Research (B) (No. 19H02722) and the Center for
Emergent Functional Matter Science at NYCU for
financial support.
12] A. D. Chowdhury, S. M. Mobin, S. Mukherjee, S. Bhaduri,
G. K. Lahiri, ‘[Pd(L)Cl ]-Catalyzed Selective Hydroxylation of
2
Arylboronic Acids to Phenols’, Eur. J. Inorg. Chem. 2011,
3
232–3239.
13] K. Inamoto, K. Nozawa, M. Yonemoto, Y. Kondo, ‘Micellar
system in copper-catalysed hydroxylation of arylboronic
acids: facile access to phenols’, Chem. Commun. 2011, 47,
Author Contribution Statement
1
1775–11777.
T. K. performed the experiments and analyzed the
data. T. K. and I. R. designed and wrote the paper.
14] H. Yang, Y. Li, M. Jiang, J. Wang, H. Fu, ‘General Copper-
Catalyzed Transformations of Functional Groups from
Arylboronic Acids in Water’, Chem. Eur. J. 2011, 17, 5652–
5
660.
[
[
15] K. Hosoi, Y. Kuriyama, S. Inagi, T. Fuchigami, ‘Electro-
chemical hydroxylation of organoboron compounds’,
Chem. Commun. 2010, 46, 1284–1286.
16] H. Jiang, L. Lykke, S. U. Pedersen, W.-J. Xiao, K. A.
Jørgensen, ‘A practical electromediated ipso-hydroxylation
of aryl and alkyl boronic acids under an air atmosphere’,
Chem. Commun. 2012, 48, 7203–7205.
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