Hydroxyl‐Directed Iridium‐Catalyzed Synthesis of Pyrano[2,3,4‐de]chromen‐2‐ones and Further Chalcogenation under Blue‐Light Irradiation DOI
Kelu Yan, Xiaoyu Wang, Jiangwei Wen

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(43)

Published: Oct. 21, 2022

Abstract The hydroxyl‐directed iridium‐catalyzed peri ‐selective C−H bond activation to synthesize substituted pyrano[2,3,4‐ de ]chromen‐2‐ones and further chalcogenylation under blue light irradiation has been realized efficiently. Most products of polycyclic pyrans corresponding chalcogenated derivatives with various substituents were achieved in good excellent yields. Preliminary mechanistic studies suggest that this transformation may pass through a five‐membered iridacycle intermediate containing an O−Ir σ‐bond photocatalytic free radical process.

Language: Английский

CH‐Functionalization of Heterocycles with the Formation of C−O, C−N, C−S/Se, and C−P Bonds by Intermolecular Addition of Heteroatom‐Centered Radicals DOI
Alexander S. Budnikov, Igor B. Krylov, Olga M. Mulina

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(11), P. 1714 - 1755

Published: April 12, 2023

Abstract In the last decade, free radicals have found a wide application in functionalization of unsaturated compounds, such as alkenes, alkynes, and arenes, via free‐radical addition to carbon‐carbon π‐bonds. these processes, intermolecular attack on aromatic substrates represents challenge due relatively high resistance π‐system reactions comparison alkene C=C bonds. The heterocycles is especially interesting diversity their structures chemical properties well importance for medicinal chemistry, agrochemistry, materials science. Addition C‐centered widely known Minisci‐type well‐reviewed. this paper, we summarized main achievements less explored group processes: by heteroatom‐centered (O‐, N‐, S‐/Se‐, P‐radicals) with emphasis papers published after 2010. Literature analysis revealed strong trend towards usage electrochemistry photoredox‐catalysis generation recent years. remaining fundamental problem field lack experimental support proposed mechanisms frequent existence several plausible reaction pathways. progress mechanistic studies can significantly improve prediction optimal conditions depending structure.

Language: Английский

Citations

14
Cobalt‐Catalyzed Double C−H Activation of Imidazopyridines with Vinylene Carbonate for the Synthesis of Pyrido[1,2‐a]benzimidazoles DOI
Min Liu,

Xinlei Sui,

Jiangwei Wen

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(47)

Published: Nov. 22, 2022

Abstract The synthesis of pyrido[1,2‐ a ]benzimidazole derivatives from the cobalt(III)‐catalyzed C−H activation and vinylene transfer imidazo[1,2‐ ]pyridines with carbonate has been proposed. Most products ]benzimidazoles were achieved in good yields under simple easy‐to‐operate conditions. Scale‐up preparation several preliminary mechanistic studies involving bond electronic effects between different substrates also performed. This protocol offers an alternative approach for diverse useful derivatives.

Language: Английский

Citations

4
C(sp2)–H selenylation of substituted benzo[4,5]imidazo[2,1-b]thiazoles using phenyliodine(iii)bis(trifluoroacetate) as a mediator DOI Creative Commons
Prasanjit Ghosh,

Gautam Chhetri,

Samir Mandal

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(7), P. 4462 - 4470

Published: Jan. 1, 2024

A metal-free regioselective C–H selenylation of substituted benzo[4,5]imidazo[2,1- b ]thiazoles is devised to prepare structurally diverse selenoether derivatives in good excellent yields. The reaction scalable and follows radical pathways.

Language: Английский

Citations

0
Rapid Access to Sulfenylated Spiro[5.5]trienones via PIFA‐promoted Dearomative Spirocyclization of Biaryl Ynones DOI
Zhichao Chen,

Yurou Feng,

Pingzhang Gao

et al.

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(34)

Published: Sept. 7, 2023

Abstract A fast and facile protocol for the sulfenylative spirocyclization of biaryl ynones employing PIFA under mild conditions is reported. range sulfenylated spiro[5.5]trienones were obtained in moderate to good yields. This transformation involves a radical process via 6‐ exo ‐trig dearomative procedure. method can be extended synthesis selenium or tellurium‐substituted spiro[5.5]trienone.

Language: Английский

Citations

0
Five-membered ring systems: with more than one N atom DOI
Larry Yet

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 281 - 332

Published: Jan. 1, 2023

Language: Английский

Citations

0
Hydroxyl‐Directed Iridium‐Catalyzed Synthesis of Pyrano[2,3,4‐de]chromen‐2‐ones and Further Chalcogenation under Blue‐Light Irradiation DOI
Kelu Yan, Xiaoyu Wang, Jiangwei Wen

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(43)

Published: Oct. 21, 2022

Abstract The hydroxyl‐directed iridium‐catalyzed peri ‐selective C−H bond activation to synthesize substituted pyrano[2,3,4‐ de ]chromen‐2‐ones and further chalcogenylation under blue light irradiation has been realized efficiently. Most products of polycyclic pyrans corresponding chalcogenated derivatives with various substituents were achieved in good excellent yields. Preliminary mechanistic studies suggest that this transformation may pass through a five‐membered iridacycle intermediate containing an O−Ir σ‐bond photocatalytic free radical process.

Language: Английский

Citations

0