Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 7, Issue 9, Pages 9028-9034Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.9b01361
Keywords
Graphene oxide; Carbocatalysis; ipso-Hydroxylation; Phenols; Boronic acids
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Funding
- University Grants Commission, New Delhi, India (UGC) [42-291/2013(SR)]
- Science and Engineering Research Board SERB, New Delhi, India [SR/FT/CS-53/2011]
- Council for Scientific and Industrial Research, New Delhi, India (CSIR) [02(0191)14/EMR-II]
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A metal-free and straightforward protocol for the synthesis of phenols from aryl and heteroaryl boronic acids has been demonstrated using graphene oxide as a carbocatalyst. This sustainable ipso-hydroxylation takes place under mild conditions using aqueous H2O2 as an oxidant in a water medium in a short time under organocatalytic and base-free conditions. The control experiments reveal that the presence of carboxyl groups promotes ipso-hydroxylation. The developed methodology offers GO as a benign solid-acid catalyst with good sustainability which can be reused several times without significant loss in its catalytic activities; this was proven by the Fourier transform infrared and powder X-ray diffraction studies of the reused catalyst.
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