Hydrogen Bonding‐Assisted Deborylative Hydroxylation of Aryl Boronic Acids via Supramolecular Catalysis

Abstract Expanding the scope of hydrogen bonding catalysis toward greener chemistry, we have devised a simple and efficient protocol for the deborylative activation of arylboronic acids for the synthesis of phenols. Utilizing the supramolecular‐hydrogen bonding catalytic behavior of cyclodextrins, a facile C─B bond cleavage was obtained for the subsequent C─O bond formation employing H 2 O 2 as an oxidant. The current protocol is organocatalytic approach, which has potential benefits over the traditional metal‐based approaches and is found to convert diverse arylboronic acids into corresponding phenols with excellent yields. The gram‐scale experiments for the synthesis of an API, guaiacol, reveals the industrial feasibility of this methodology.

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Journal
ChemistrySelect
Published
2025-08-01
DOI
https://doi.org/10.1002/slct.202501154
Primary Topic
Organoboron and organosilicon chemistry
Type
article
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0.00
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article

Hydrogen Bonding‐Assisted Deborylative Hydroxylation of Aryl Boronic Acids via Supramolecular Catalysis

Abhinandan Chopada, Sheik Haseena, Sandip J. Detke, Sai Srinivas Ponugoti et al.
ChemistrySelect
Organoboron and organosilicon chemistry
article

Hydrogen Bonding‐Assisted Deborylative Hydroxylation of Aryl Boronic Acids via Supramolecular Catalysis

Abhinandan Chopada, Sheik Haseena, Sandip J. Detke, Sai Srinivas Ponugoti, Shreerang V. Joshi, Prashant S. Kharkar, Aditya Lade, Abhishek Kardile, Ankita A. Kanhere
article en

Abstract

Abstract Expanding the scope of hydrogen bonding catalysis toward greener chemistry, we have devised a simple and efficient protocol for the deborylative activation of arylboronic acids for the synthesis of phenols. Utilizing the supramolecular‐hydrogen bonding catalytic behavior of cyclodextrins, a facile C─B bond cleavage was obtained for the subsequent C─O bond formation employing H 2 O 2 as an oxidant. The current protocol is organocatalytic approach, which has potential benefits over the traditional metal‐based approaches and is found to convert diverse arylboronic acids into corresponding phenols with excellent yields. The gram‐scale experiments for the synthesis of an API, guaiacol, reveals the industrial feasibility of this methodology.

ChemistrySelectVol. 10(31)
Institute of Chemical Technology (IN), SRM University (IN)
Openalex Percentile: Top 84%
Organoboron and organosilicon chemistry
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Hydrogen Bonding‐Assisted Deborylative Hydroxylation of Aryl Boronic Acids via Supramolecular Catalysis — Abhinandan Chopada, Sheik Haseena, et al. · ChemistrySelect (2025) | TGRS Research Map | TGRS