Photo- or Electrochemical Cyclization of Dienes with Diselenides to Access Seleno-Benzo[b]azepines DOI

Pengpeng Tan,

Liwang Lu,

Shilong Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7245 - 7255

Published: May 23, 2023

A cascade selenylation/cyclization of dienes with diselenides has been realized under visible-light irradiation or electrolysis conditions. Employing O2 electricity as a "green" oxidant, this protocol provides green and efficient method for an array biologically important seleno-benzo[b]azepine derivatives in moderate to good yields. The direct sunlight gram-scale reaction render the approach practical attractive.

Language: Английский

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts DOI Creative Commons
Daniel Kaiser, Immo Klose,

Rik Oost

et al.

Chemical Reviews, Journal Year: 2019, Volume and Issue: 119(14), P. 8701 - 8780

Published: June 25, 2019

Organosulfur compounds have long played a vital role in organic chemistry and the development of novel chemical structures architectures. Prominent among these organosulfur are those involving sulfur(IV) center, which been subject countless investigations over more than hundred years. In addition to list textbook sulfur-based reactions, there has sustained interest organosulfur(IV) recent Of particular within is ease with synthetic chemist can effect wide range transformations through either bond formation or cleavage at sulfur. This review aims cover developments past decade molecules provide insight into both reactions critically rely on this versatile element diverse scaffolds that thereby be synthesized.

Language: Английский

Citations

698

Recent advances in cascade radical cyclization of radical acceptors for the synthesis of carbo- and heterocycles DOI

Jianhua Liao,

Xiao Yang, Lu Ouyang

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(6), P. 1345 - 1363

Published: Jan. 1, 2021

This review is devoted to highlighting main achievements in the development of cascade radical cyclization acceptors for synthesis carbo- and heterocycles.

Language: Английский

Citations

146

Visible-light-induced three-component reaction of quinoxalin-2(1H)-ones, alkenes and CF3SO2Na leading to 3-trifluoroalkylated quinoxalin-2(1H)-ones DOI
Na Meng,

Yufen Lv,

Qishun Liu

et al.

Chinese Chemical Letters, Journal Year: 2020, Volume and Issue: 32(1), P. 258 - 262

Published: Nov. 20, 2020

Language: Английский

Citations

142

Recent Advances in Radical‐Enabled Bicyclization and Annulation/1,n‐Bifunctionalization Reactions DOI Open Access

Minhua Huang,

Wen‐Juan Hao, Bo Jiang

et al.

Chemistry - An Asian Journal, Journal Year: 2018, Volume and Issue: 13(20), P. 2958 - 2977

Published: Aug. 15, 2018

Over the past few years, development of new radical reactions has gained considerable momentum. Most such transformations heavily depend on in situ generation reactive species, initiated by oxidants, metal salts, visible-light photocatalysis, or electrocatalysis. In this context, numerous radical-enabled bicyclization and annulation/1,n-bifunctionalization have been developed, thereby providing efficient synthetic strategies for assembly functionalized cyclic rings that contain both heterocyclic isocyclic skeletons. Focus Review, we highlight recent progress rapidly growing area presenting a series catalytic oxidative reactions, along with their reaction mechanisms applications.

Language: Английский

Citations

142

Visible-light-induced metal and reagent-free oxidative coupling of sp2 C–H bonds with organo-dichalcogenides: synthesis of 3-organochalcogenyl indoles DOI
Vandana Rathore, Sangit Kumar

Green Chemistry, Journal Year: 2019, Volume and Issue: 21(10), P. 2670 - 2676

Published: Jan. 1, 2019

Here, a unique visible-light-induced method for the organochalcogenation of sp2 C–H bonds indoles and aniline has been presented using diaryl dichalcogenides (S, Se, Te) oxygen as an oxidant avoiding photocatalyst, base, catalyst, reagent in acetone.

Language: Английский

Citations

117

Direct C−H Trifluoromethylation of Quinoxalin‐2(1H)‐ones under Transition‐Metal‐Free Conditions DOI
Liping Wang, Yuecheng Zhang, Fanfan Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2018, Volume and Issue: 360(20), P. 3969 - 3977

Published: Aug. 3, 2018

Abstract Disclosed herein is a direct C−H trifluoromethylation of quinoxalin‐2(1 H )‐ones with sodium trifluoromethanesulfinate. This protocol affords series 3‐trifluoromethylquinoxalin‐2(1 )‐one derivatives in moderate to excellent yields under transition‐metal‐free conditions. The present methodology features utilization the inexpensive trifluoromethyl source without transition‐metal‐catalysts, mild reaction conditions and high functional group tolerance, which promises convenient efficient access pharmaceutically interesting quinoxalinones. magnified image

Language: Английский

Citations

115

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry DOI Creative Commons
Michael K. Bogdos,

Emmanuel Pinard,

John A. Murphy

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2018, Volume and Issue: 14, P. 2035 - 2064

Published: Aug. 3, 2018

The focus of this review is to provide an overview the field organocatalysed photoredox chemistry relevant synthetic medicinal chemistry. Photoredox transformations have been shown enable key that are important pharmaceutical industry. This type has also demonstrated a high degree sustainability, especially when organic dyes can be employed in place often toxic and environmentally damaging transition metals. sections arranged according general class presented reactions value these methods considered. An characteristics photocatalysts as well some electrochemical data presented. In addition, reaction mechanisms for discussed individual mechanistic considerations highlighted text appropriate.

Language: Английский

Citations

112

Metal-free visible-light-induced oxidative cyclization reaction of 1,6-enynes and arylsulfinic acids leading to sulfonylated benzofurans DOI
Leilei Wang, Min Zhang, Yulong Zhang

et al.

Chinese Chemical Letters, Journal Year: 2019, Volume and Issue: 31(1), P. 67 - 70

Published: May 24, 2019

Language: Английский

Citations

102

PQS-enabled visible-light iridium photoredox catalysis in water at room temperature DOI
Mei‐jie Bu, Chun Cai, Fabrice Gallou

et al.

Green Chemistry, Journal Year: 2018, Volume and Issue: 20(6), P. 1233 - 1237

Published: Jan. 1, 2018

A new photocatalyst attached to the designer surfactant PQS has been developed that self-aggregates into micelles, thereby enabling photoredox catalysis conducted in water at room temperature without any additives or co-solvents.

Language: Английский

Citations

96

Bromide-catalyzed electrochemical trifluoromethylation/cyclization of N-arylacrylamides with low catalyst loading DOI

Yangye Jiang,

Gui-Yuan Dou,

Kun Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2018, Volume and Issue: 5(17), P. 2573 - 2577

Published: Jan. 1, 2018

An electro-generated trifluoromethyl radical mediated by a bromide ion is efficiently applied to the trifluoromethylarylation/cyclization of N-arylacrylamides.

Language: Английский

Citations

95