Photo- and Electrochemical Organic Transformations Involving Radical Pathway: A Retrospection of Our Green-Chemistry-Inspired Synthetic Endeavours

Dedicated to Professor Brindaban C. Ranu on the occasion of his 75^th Birthday

Abstract

This account summarises our recent efforts (2020 to mid-2024) in designing and developing a handful of promising organic transformations for accessing several diversely functionalized biologically relevant organic scaffolds by following the green-chemistry principles with a particular focus on the application of low-energy visible light and electrochemistry. Mechanistic studies of each of these reactions established the involvement of a radical pathway.

1 Introduction

2 Green-Inspired Organic Transformations

2.1 Visible-Light-Driven Organic Synthesis

2.1.1 Synthesis of Functionalized Dihydrofuro[3,2-c]chromenones

2.1.2 Synthesis of Functionalized 2-(Aryl/alkylamino)-3-(aryl/alkylselanyl)naphthalene-1,4-diones and 2-(Arylamino)-3-(arylthio)naphthalene-1,4-diones

2.1.3 Synthesis of Functionalized 6-(Arylthio/arylseleno)benzo[a]phenazin-5-ols

2.1.4 Synthesis of Functionalized 3-(Alkyl/benzylthio)-4-hydroxy-2H-chromen-2-ones

2.1.5 Synthesis of Functionalized 2-Hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxamides and 2-Hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxylates

2.1.6 Synthesis of Functionalized 2-Hydroxyphenylated α-Ketoamides

2.2 Electrochemical Organic Synthesis

2.2.1 Synthesis of 3-Selenylated/Sulfenylated Derivatives of 2-Amino-1,4-naphthoquinones

2.2.2 Synthesis of Functionalized 6-(Arylthio/Arylseleno)benzo[a]phenazin-5-ols

2.2.3 Synthesis of Functionalized Alkyl 2-Hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxylates

3 Conclusions

Key words

photochemistry - visible light - electrochemistry - electrosynthesis - radical mechanistic pathway - green chemistry

Publication History

Received: 22 May 2024

Accepted after revision: 19 June 2024

Article published online:
08 July 2024

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