Synthesis of Fluoromethylated Chromones and Their Heteroatom Analogues via Sodium Fluoromethanesulfinate-Enabled Direct Fluoromethylation DOI

Kaiyue Yang,

Dongxue Yin,

Yuli Sun

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 565 - 575

Published: Dec. 20, 2023

An array of biologically interesting tri/difluoromethylated chromones and their heteroatom analogues were conveniently synthesized from the reaction with CF3SO2Na or HCF2SO2Na in presence tert-butyl hydroperoxide under mild conditions. A mechanistic pathway involving generation electrophilic tri/difluoromethyl radical, followed radical substitution analogues, was postulated.

Language: Английский

Photoinduced, additive- and photosensitizer-free multi-component synthesis of naphthoselenazol-2-amines with air in water DOI

Hong‐Tao Ji,

Keli Wang, Wen‐Tao Ouyang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 7983 - 7987

Published: Jan. 1, 2023

An atom- and step-economical, efficient eco-friendly method for constructing naphthoselenazol-2-amines through a visible-light photocatalytic multi-component reaction under aqueous phase conditions is reported.

Language: Английский

Citations

76

Recent advances on electrochemical generation of sulfonyl radical triggered cyclization of alkene/alkynes DOI

Jiaqing Shao,

Jiang Liu, Haibo Mei

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: 173, P. 134467 - 134467

Published: Jan. 12, 2025

Language: Английский

Citations

3

Metal‐Free Electrochemical Trifluoromethylation of Imidazole‐Fused Heterocycles with Trifluoromethyl Thianthrenium Triflate DOI
Chang Ge,

Lipeng Qiao,

Yuyang Zhang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(15), P. 1679 - 1685

Published: March 15, 2024

Comprehensive Summary A novel and eco‐friendly electrochemical activation of trifluoromethyl thianthrenium triflate (TT–CF 3 + OTf − ) for trifluoromethylation imidazole‐fused heteroaromatic compounds was established. This method involves the direct electrolysis TT–CF without requirement external oxidants or catalysts, aligning with principles green chemistry. wide range including imidazo[1,2‐ a ]pyridines benzo[ d ]imidazo[2,1‐ b ]thiazoles have been successfully trifluoromethylated using this technique, exhibiting excellent compatibility various functional groups broad substrate scope. Moreover, method's applicability one‐pot sequential reactions enables reduction waste resource consumption by eliminating need intermediate purification steps.

Language: Английский

Citations

11

Visible-Light Induced Organophotocatalysis for the Synthesis of Difluoroethylated Benzoxazines DOI Open Access
Xiang Chen, Wen‐Tao Ouyang, Xiao Li

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(12), P. 4213 - 4213

Published: Jan. 1, 2023

Benzoxazines are important motif in pharmaceuticals and functional molecules.A visible-light induced photocatalytic strategy for the synthesis of difluoroethyl benzoxazines with organo-photocatalyst was developed.In present protocol, a series olefinic amides can be transferred to difluoroethylated via oxydifluoromethylation CF2HSO2Na as difluoromethylating reagent, which is easily operated good group tolerant.

Language: Английский

Citations

22

Paraformaldehyde as C1 Synthon: Electrochemical Three‐Component Synthesis of Tetrahydroimidazo[1,5‐a]quinoxalin‐4(5H)‐ones in Aqueous Ethanol DOI
Yuhan Lu,

Si‐Yu Mu,

Jun Jiang

et al.

ChemSusChem, Journal Year: 2023, Volume and Issue: 16(19)

Published: Sept. 20, 2023

A green and practical method for the electrochemical synthesis of tetrahydroimidazo[1,5-a]quinoxalin-4(5H)-ones through three-component reaction quinoxalin-2(1H)-ones, N-arylglycines paraformaldehyde was reported. In this strategy, EtOH played dual roles (eco-friendly solvent waste-free pre-catalyst) in situ generated ethoxide promoted triple sequential deprotonations.

Language: Английский

Citations

17

Accessing 3,4-Dihydroquinolinone from N-Arylacrylamides via Tetralone-Mediated Energy Transfer and 1,3-Hydrogen Shift DOI

Yongbo Tan,

Jing Zhao, Guo‐Jun Deng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2398 - 2402

Published: March 18, 2024

Herein, we introduce a tetralone-mediated photocyclization method of N-arylacrylamides. The protocol proceeds smoothly to deliver diverse set 3,4-dihydroquinolinones in moderate good yields with excellent functional group compatibility and readily allows for late-stage modifications number complex drug molecules. Mechanistic studies reveal that the present systems ultraviolet light irradiation enable cyclization via energy transfer exclusive 1,3-hydrogen shift.

Language: Английский

Citations

6

Visible Light-Induced Radical Cascade Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Polycyclic Imidazoles DOI Creative Commons
S.J. Lin, Yuanyuan Deng,

Hanxun Zhong

et al.

ACS Omega, Journal Year: 2024, Volume and Issue: 9(26), P. 28129 - 28143

Published: June 19, 2024

An efficient and mild protocol for the visible light-induced radical cascade difluoromethylation/cyclization of imidazoles with unactivated alkenes using easily accessible bench-stable difluoromethyltriphenylphosphonium bromide as precursor -CF

Language: Английский

Citations

5

Introduction of Difluoromethyl through Radical Pathways DOI
Xin Li, Qiuling Song

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(31)

Published: June 5, 2024

Abstract During the past decade, radical difluoromethylation has emerged as a powerful and versatile tool for incorporation of difluoromethyl into various organic compounds. These reactions feature mild reaction conditions, very good functional group compatibilities, quite broad substrate scopes, thus having drawn much attention got rapid developments. A diverse range precursors have been developed series reactions. This review summarizes discusses advance in reactions, which are organized according to protocols generating radical.

Language: Английский

Citations

4

Photoelectrochemical synthesis of 4-halomethyl benzoxazines with a halogen anion source DOI
Xiang Chen,

Xiao Li,

Hui Dai

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5553 - 5557

Published: Jan. 1, 2024

A mild and efficient protocol for preparing 4-halomethyl benzoxazines via a photoelectrochemical process with ammonium halide as the halogenating reagent was developed.

Language: Английский

Citations

4

Electrochemical deoxygenative amination of stabilized alkyl radicals from activated alcohols DOI Creative Commons

Jia Xu,

Yilin Liu, Qing Wang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: July 20, 2024

Alkylamine structures represent one of the most functional and widely used in organic synthesis drug design. However, general methods for functionalization shielded deshielded alkyl radicals remain elusive. Here, we report a deoxygenative amination protocol using alcohol-derived carbazates nitrobenzene under electrochemical conditions. A range primary, secondary, tertiary alkylamines are obtained. This practical procedure can be scaled up through continuous flow technique.

Language: Английский

Citations

3