Recent advances in C–H functionalisation through indirect hydrogen atom transfer

Filip S. Meger, John A. Murphy

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)
16 Downloads (Pure)

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.
Original languageEnglish
Article number6127
Number of pages83
JournalMolecules
Volume28
Issue number16
DOIs
Publication statusPublished - 18 Aug 2023

Keywords

  • hydrogen atom transfer
  • functionalisation
  • radicals
  • photoredox
  • electrochemistry

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