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Review

Recent Advances in C–H Functionalisation through Indirect Hydrogen Atom Transfer †

by
Filip S. Meger
1,* and
John A. Murphy
2,*
1
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, 16 Avinguda dels Països Catalans, 43007 Tarragona, Catalonia, Spain
2
Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, UK
*
Authors to whom correspondence should be addressed.
†
In honour of Professor John C Walton for his extensive contributions to radical chemistry.
Molecules 2023, 28(16), 6127; https://doi.org/10.3390/molecules28166127
Submission received: 23 July 2023 / Revised: 9 August 2023 / Accepted: 15 August 2023 / Published: 18 August 2023
(This article belongs to the Special Issue Radicals, Mechanisms and Synthesis: A Themed Issue in Honor of the Many Contributions of Prof. Dr. John C. Walton)
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Abstract

The functionalisation of C–H bonds has been an enormous achievement in synthetic methodology, enabling new retrosynthetic disconnections and affording simple synthetic equivalents for synthons. Hydrogen atom transfer (HAT) is a key method for forming alkyl radicals from C–H substrates. Classic reactions, including the Barton nitrite ester reaction and Hofmann–Löffler–Freytag reaction, among others, provided early examples of HAT. However, recent developments in photoredox catalysis and electrochemistry have made HAT a powerful synthetic tool capable of introducing a wide range of functional groups into C–H bonds. Moreover, greater mechanistic insights into HAT have stimulated the development of increasingly site-selective protocols. Site-selectivity can be achieved through the tuning of electron density at certain C–H bonds using additives, a judicious choice of HAT reagent, and a solvent system. Herein, we describe the latest methods for functionalizing C–H/Si–H/Ge–H bonds using indirect HAT between 2018–2023, as well as a critical discussion of new HAT reagents, mechanistic aspects, substrate scopes, and background contexts of the protocols.
Keywords: hydrogen atom transfer; functionalisation; radicals; photoredox; electrochemistry; catalysis hydrogen atom transfer; functionalisation; radicals; photoredox; electrochemistry; catalysis
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MDPI and ACS Style

Meger, F.S.; Murphy, J.A. Recent Advances in C–H Functionalisation through Indirect Hydrogen Atom Transfer. Molecules 2023, 28, 6127. https://doi.org/10.3390/molecules28166127

AMA Style

Meger FS, Murphy JA. Recent Advances in C–H Functionalisation through Indirect Hydrogen Atom Transfer. Molecules. 2023; 28(16):6127. https://doi.org/10.3390/molecules28166127

Chicago/Turabian Style

Meger, Filip S., and John A. Murphy. 2023. "Recent Advances in C–H Functionalisation through Indirect Hydrogen Atom Transfer" Molecules 28, no. 16: 6127. https://doi.org/10.3390/molecules28166127

APA Style

Meger, F. S., & Murphy, J. A. (2023). Recent Advances in C–H Functionalisation through Indirect Hydrogen Atom Transfer. Molecules, 28(16), 6127. https://doi.org/10.3390/molecules28166127

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