Ascorbic Acid as a Highly Efficient Organocatalyst for <i>ipso</i>‐Hydroxylation of Arylboronic Acid

Das, Sameeran Kumar; Bhattacharjee, Prantika; Bora, Utpal

doi:10.1002/slct.201703036

Cited by 24 publications

(12 citation statements)

References 46 publications

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“…In particular, during recent times aerial oxygen mediated approaches towards the synthesis of phenolic derivatives have found greater value in synthetic organic chemistry. These methods are using benzoquinone, gallic acid, ascorbic acid and rose bengal as organocatalysts for the ipso ‐hydroxylation of boronic acids. Also, it was reported that the aerial oxygen can be introduced as an oxidant to accomplish the desired chemical transformations –––.…”

Section: Methodsmentioning

confidence: 99%

Amino‐Acid‐Mediated Aerobic Oxidation of Organoborons for the Synthesis of Phenolic Derivatives Using Single Electron Transfer

et al. 2020

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An efficient amino‐acid‐mediated ipso‐hydroxylation of arylboronic acids, aryl boronate esters and aryl trifluoroborates to aryl alcohols has been described. The current protocol was realized by using sub‐stoichiometric amount of l‐histidine in presence of triethylamine under aerobic conditions in DMF as solvent. This amino‐acid‐mediated process provides an alternative route for the hydroxylation of organoborons through in situ generation of hydrogen peroxide. The present protocol explores the synthetic utility of amino acids as organocatalysts for the preparation of aryl alcohols. It was observed that l‐histidine plays an important role for the conversion of aerial oxygen in to hydrogen peroxide via thermal excitation process followed by thermal degradation of Et3N. The developed approach holds good for a wide range of compounds with excellent yields and competent functional group tolerance.

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Section: Methodsmentioning

confidence: 99%

Amino‐Acid‐Mediated Aerobic Oxidation of Organoborons for the Synthesis of Phenolic Derivatives Using Single Electron Transfer

et al. 2020

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“…Still, the methodology took a longer reaction time, and a low yield of the desired product was obtained [19] . Sequentially, further advancement in the catalytic system has been progressed, and a wide array of the non‐metallic catalytic system has been developed, which utilized WERSA‐H 2 O 2 , [25] ascorbic acid‐H 2 O 2 , [26] TBHP‐KOH, [20] and N ‐oxide [23] . Recently, He group reported microwave‐assisted aerobic hydroxylation of boronic acid using KOH and DMSO [27] .…”

Section: Figurementioning

confidence: 99%

Highly efficient heterogeneous V₂O₅@TiO₂ catalyzed the rapid transformation of boronic acids to phenols

2021

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A V2O5@TiO2 catalyzed green and efficient protocol for the hydroxylation of boronic acid into phenol has been developed utilizing environmentally benign oxidant hydrogen peroxide. A wide range of electron‐donating and the electron‐withdrawing group‐containing (hetero)aryl boronic acids were transformed into their corresponding phenol. The methodology was also applied successfully to transform various natural and bioactive molecules like tocopherol, amino acids, cinchonidine, vasicinone, menthol, and pharmaceuticals such as ciprofloxacin, ibuprofen, and paracetamol. The other feature of the methodology includes gram‐scale synthetic applicability, recyclability, and short reaction time.

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“…The catalytic system was proved to be effective even after five cycles without significant loss of activity. Recently, the same group reported that ascorbic acid could act as a highly efficient organocatalyst for the hydroxylation of aryl boronic acids (Scheme a) …”

Section: Thermal Catalytic Conversion Of Aryl Boronic Compounds Tomentioning

confidence: 99%

Recent Advances in Green Synthesis of Functionalized Phenols from Aromatic Boronic Compounds

et al. 2019

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Phenol and its derivatives are fundamental building blocks in organic synthesis and materials science. Over the past decades, tremendous attention has been paid to construct functionalized phenols, and various methods have been developed. Owing to the high efficiency and mild reaction conditions, synthesis of phenols from the hydroxylation of aryl boronic compounds has been emerging as a promising approach. In this review, we summarize the progress using aryl boronic compounds as starting reagents to synthesize phenol deriva- [a]

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Ascorbic Acid as a Highly Efficient Organocatalyst for ipso‐Hydroxylation of Arylboronic Acid

Cited by 24 publications

References 46 publications

Amino‐Acid‐Mediated Aerobic Oxidation of Organoborons for the Synthesis of Phenolic Derivatives Using Single Electron Transfer

Amino‐Acid‐Mediated Aerobic Oxidation of Organoborons for the Synthesis of Phenolic Derivatives Using Single Electron Transfer

Highly efficient heterogeneous V₂O₅@TiO₂ catalyzed the rapid transformation of boronic acids to phenols

Recent Advances in Green Synthesis of Functionalized Phenols from Aromatic Boronic Compounds

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Ascorbic Acid as a Highly Efficient Organocatalyst for ipso‐Hydroxylation of Arylboronic Acid

Cited by 24 publications

References 46 publications

Amino‐Acid‐Mediated Aerobic Oxidation of Organoborons for the Synthesis of Phenolic Derivatives Using Single Electron Transfer

Amino‐Acid‐Mediated Aerobic Oxidation of Organoborons for the Synthesis of Phenolic Derivatives Using Single Electron Transfer

Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols

Recent Advances in Green Synthesis of Functionalized Phenols from Aromatic Boronic Compounds

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Highly efficient heterogeneous V₂O₅@TiO₂ catalyzed the rapid transformation of boronic acids to phenols