Recent Advances in C–H Functionalisation through Indirect Hydrogen Atom Transfer DOI Creative Commons
Filip S. Meger, John A. Murphy

Molecules, Journal Year: 2023, Volume and Issue: 28(16), P. 6127 - 6127

Published: Aug. 18, 2023

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

Language: Английский

Metal-Free Photosynthesis of Alkylated Benzimidazo[2,1-a]isoquinoline-6(5H)-ones and Indolo[2,1-a]isoquinolin-6(5H)-ones in PEG-200 DOI

Hao‐Cong Li,

Kai Sun, Xiang Li

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(13), P. 9055 - 9066

Published: June 23, 2021

A visible-light-induced decarboxylation reaction was developed for the synthesis of alkylated benzimidazo[2,1-a]isoquinoline-6(5H)-ones and indolo[2,1-a]isoquinolin-6(5H)-ones under metal-free conditions. Impressively, metal catalysts traditionally volatile organic solvents could be effectively avoided.

Language: Английский

Citations

58

Alkyl/Glycosyl Sulfoxides as Radical Precursors and Their Use in the Synthesis of Pyridine Derivatives** DOI

Demeng Xie,

Yingwei Wang, Xia Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(31)

Published: June 1, 2022

We report here the use of simple and readily available alkyl sulfoxides as precursors to radicals their application in preparation pyridine derivatives. show that sulfoxides, N-methoxy pyridinium salts fluoride anions form electron donor-acceptor (EDA) complexes solution, which, upon visible light irradiation, undergo a radical chain process afford various derivatives smoothly. This reaction displays broad scope with respect both pyridiniums. The synthetic versatility handle chemistry adds power precursors. Glycosyl are converted corresponding pyridyl C-glycosides high stereoselectivities. Computational experimental studies provide insights into mechanism.

Language: Английский

Citations

53

Three-component reaction access to S-alkyl dithiocarbamates under visible-light irradiation conditions in water DOI

Xuehao Li,

Wenwen Cui,

Qirong Deng

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(3), P. 1302 - 1307

Published: Jan. 1, 2022

An environmentally friendly multicomponent reaction protocol to synthesize S -alkyl dithiocarbamate derivatives from Katritzky salt, CS 2 , and secondary amines under visible light irradiation conditions has been developed.

Language: Английский

Citations

47

Recent Progress in Fragmentation of Katritzky Salts Enabling Formation of C–C, C–B, and C–S Bonds DOI
Yuan Gao, Songwei Jiang,

Nian‐Dong Mao

et al.

Topics in Current Chemistry, Journal Year: 2022, Volume and Issue: 380(4)

Published: May 19, 2022

Language: Английский

Citations

39

Recent Advances in C–H Functionalisation through Indirect Hydrogen Atom Transfer DOI Creative Commons
Filip S. Meger, John A. Murphy

Molecules, Journal Year: 2023, Volume and Issue: 28(16), P. 6127 - 6127

Published: Aug. 18, 2023

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

Language: Английский

Citations

29