Metal free visible light photoredox activation of PhI(OAc)2 for the conversion of arylboronic acids to phenols

Paul, Abhijit; Chatterjee, Debnath; Rajkamal,; Halder, Tanmoy; Banerjee, Srirupa; Yadav, Somnath

doi:10.1016/j.tetlet.2015.03.107

Cited by 40 publications

(21 citation statements)

References 33 publications

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“…The mechanism of the reaction appears to be complex and could proceed through the pathway outlined in Scheme 7. 46 Initially, the boronic acid reacts to form the boronate salt, CO 2 and H 2 O which coordinates to the former. Electron transfer from the photoexcited eosin Y to PhI(OAc) 2 leads to the formation of an CH 3 COO À and a CH 3 radical.…”

Section: Oxidative Transformation Of Phenylboronic Acid To Phenolmentioning

confidence: 99%

Eosin Y catalysed photoredox synthesis: a review

Srivastava¹,

Singh²

2017

RSC Adv.

307

176

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Section: Oxidative Transformation Of Phenylboronic Acid To Phenolmentioning

confidence: 99%

Eosin Y catalysed photoredox synthesis: a review

Srivastava¹,

Singh²

2017

RSC Adv.

307

176

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“…In 2015, Yadav and co-workers reported the conversion of arylboronic acids 101 to corresponding phenols 103 by using organic photoredox catalysis under mild reaction conditions. 97 During these transformations, the organic dye eosin Y 78 was used as photoredox catalyst and PhI(OAc)2 102 was used to generate the radical species. All the reactions were performed in the presence of visible light and functionalized phenols 103 were isolated in excellent yields (Scheme 35).…”

Section: Conversion Of Arylboronic Acids To Phenolsmentioning

confidence: 99%

Hypervalent iodine chemistry and light: photochemical reactions involving hypervalent iodine chemistry

Singh¹,

Wirth²

2021

Arkivoc

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Chemistry of hypervalent iodine reagents have developed extensively after the discovery of IBX as a commercial reagent in organic synthesis. Their stability in air, environmentally nature and unique reactivity under mild reaction conditions makes them more suitable reagents for medicinal and natural product chemistry. Various synthetic transformations have been achieved by using hypervalent iodine reagents under mild reaction conditions. Hypervalent iodine catalysis is identified as an emerging research area in past couple of decades. In past few years, hypervalent iodine reagents have found their application in photoredox catalysis. In this review article, the progress of photoredox catalysis by involving hypervalent iodine reagents would be covered.

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“…In 2015, Yadav and co‐workers reported the visible light photoredox activation of PhI(OAc) 2 by an organocatalytic methodology using eosin Y (Scheme ) . The methodology was successfully applied in the conversion of aryl boronic acids to phenols.…”

Section: Photocatalytic Conversion Of Aryl Boronic Compounds To Phmentioning

confidence: 99%

“…Plausible mechanism for light catalyzed hydroxylation by eosin Y and PhI(OAc) 2 . Adapted from ref . Copyright (2015), with permission from Elsevier.…”

Section: Photocatalytic Conversion Of Aryl Boronic Compounds To Phmentioning

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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Metal free visible light photoredox activation of PhI(OAc)2 for the conversion of arylboronic acids to phenols

Cited by 40 publications

References 33 publications

Eosin Y catalysed photoredox synthesis: a review

Eosin Y catalysed photoredox synthesis: a review

Hypervalent iodine chemistry and light: photochemical reactions involving hypervalent iodine chemistry

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

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