Metal- and base-free regioselective cascade sulfonylation-cyclization of 1,5-dienes via the insertion of sulfur dioxide: access to pyrrolinones DOI
Ran Ding,

Xue-Feng Tang,

Yu-Hang Deng

et al.

New Journal of Chemistry, Journal Year: 2022, Volume and Issue: 46(27), P. 12901 - 12904

Published: Jan. 1, 2022

A metal- and base-free regioselective cascade sulfonylation–cyclization reaction of linear substrates, 1,5-dienes, has been developed to synthesize sulfonylated pyrrolinones.

Language: Английский

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency DOI
Guglielmo Coppola, Serena Pillitteri, Erik V. Van der Eycken

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(6), P. 2313 - 2382

Published: Jan. 1, 2022

Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The versatility of photocatalyzed reactions already demonstrated be effective providing alternative routes for cross-coupling well multicomponent reactions. photocatalyst allows generation high-energy intermediates through light irradiation rather than using highly reactive reagents or harsh reaction conditions. In a similar vein, electrochemistry experienced fruitful renaissance generating without need any catalyst. Such milder approaches pose basis toward higher selectivity and broader applicability. electrochemical reactions, species acts starter cascade events. This diverse reactivity use is usually not covered by classical methods. Owing availability cheaper more standardized photo- reactors, easily scalable flow-setups, it surprising that these two fields have become areas increased research interest. Keeping view, this review aimed at overview synthetic design MCRs involving and/or activation crucial step with particular focus on choice difunctionalized reagent.

Language: Английский

Citations

163

Photoinduced radical-polar crossover cyclization reactions DOI
Zhiming Zhu, Yongxin Zhang, Ziyang Li

et al.

Chem Catalysis, Journal Year: 2024, Volume and Issue: 4(5), P. 100945 - 100945

Published: March 5, 2024

Language: Английский

Citations

14

Construction of sulfonated spiro[5,5]trienones from sulfur dioxide via iron-catalyzed dearomative spirocyclization of biaryls DOI
Fu‐Sheng He,

Lingjing Su,

Feiyan Yu

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(7), P. 1937 - 1942

Published: Jan. 1, 2022

An iron-catalyzed dearomative spirocyclization of biaryl ynones with sodium metabisulfite and cycloketone oxime esters is developed for the construction sulfonated spiro[5,5]trienones.

Language: Английский

Citations

29

Multicomponent Sulfonylation of Alkenes to Access β-Substituted Arylsulfones DOI

Kai‐Yi Zhang,

Fang Long,

Chuan‐Chong Peng

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3772 - 3780

Published: March 6, 2023

A novel multicomponent sulfonylation of alkenes is described for the assembly various β-substituted arylsulfones using cheap and easily available K2S2O5 as a sulfur dioxide source. Of note, procedure does not need any extra oxidants metal catalysts exhibits relatively wide substrate scope good functional group compatibility. Mechanistically, an initial arylsulfonyl radical formed involving insertion with aryl diazonium salt, followed by alkoxyarylsulfonylation or hydroxysulfonylation alkenes.

Language: Английский

Citations

17

The synthesis of seven- and eight-membered rings by radical strategies DOI

Xuan-Chi Yu,

Cancan Zhang,

Ling‐Tao Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(17), P. 4757 - 4781

Published: Jan. 1, 2022

Radical strategies for preparation of seven- or eight-membered rings.

Language: Английский

Citations

26

Visible-Light-Induced Difluoroalkylation of 1-(Allyloxy)-2-(1-arylvinyl)benzenes and 1-(1-Arylvinyl)-2-(vinyloxy)benzenes: Synthesis of Bis-Difluoroalkylated Benzoxepines and 2H-Chromenes DOI
Nengneng Zhou,

Ziqin Xia,

Kaimo Kuang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(31), P. 5791 - 5796

Published: Aug. 2, 2022

A novel visible-light-mediated difluoroalkylation of 1-(allyloxy)-2-(1-arylvinyl)benzenes and 1-(1-arylvinyl)-2-(vinyloxy)benzenes for the synthesis bis-difluoroalkylated benzoxepines 2H-chromenes is developed. This method features mild reaction conditions, good regioselectivity, a wide substrate scope, functional-group compatibility, late-stage modification. Preliminary mechanistic studies reveal that generation CF2CO2Et radical more prone to with double bond aryl group.

Language: Английский

Citations

20

Visible-Light-Promoted Cyanoalkylation/Cyclization Cascade Reaction to Assemble Polyheterocycles in Continuous Flow DOI

Shan‐Shan Zhu,

Ji-Kang Liu,

Long‐Zhou Qin

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(4), P. 2057 - 2068

Published: Jan. 30, 2023

This study describes a visible-light-induced cascade reaction for preparing cyanoalkyl-containing polyheterocycles initiated by the photoinduced radical addition of N-arylacrylamide derivatives using cyclic oxime esters as sources followed cyanoalkyl-mediated cyclization. protocol features outstanding functional group compatibility, providing variety desired phenanthridine in moderate to good yields. Moreover, application microflow technique enhanced these reactions compared with equivalent batch reaction, significantly reducing times 10 min.

Language: Английский

Citations

13

NHC-Catalyzed Regioselective Intramolecular Radical Cyclization Reaction for the Synthesis of Benzazepine Derivatives DOI
Nengneng Zhou,

Fangli Zhao,

Lei Wang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(32), P. 6072 - 6076

Published: Aug. 8, 2023

A novel and efficient strategy for the synthesis of a series structurally interesting benzazepine derivatives via an N-heterocyclic carbene-catalyzed regioselective intramolecular radical cyclization has been developed. This protocol features good regioselectivity, functional-group compatibility, wide substrate scope, providing transition-metal- oxidant-free pathway to access seven-membered rings under mild reaction conditions. Additionally, further transformation benzazepines large-scale experiment were also conducted.

Language: Английский

Citations

12

Palladium-catalyzed radical cascade cyanoalkylsulfonylation/cyclization of 3-arylethynyl-[1,1′-biphenyl]-2-carbonitriles with cyclobutanone oxime esters and DABSO DOI
Nengneng Zhou,

Qiankun Xu,

Ziqin Xia

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(14), P. 2335 - 2338

Published: Jan. 1, 2022

A palladium-catalyzed radical cascade cyanoalkylsulfonylation/cyclization of 3-arylethynyl-[1,1'-biphenyl]-2-carbonitriles with DABCO·(SO2)2 and cyclobutanone oxime esters via cleavage a C-C single bond insertion SO2 was described. series cyanoalkylsulfone-containing cyclopenta[gh]phenanthridines were obtained in moderate-to-good yields, thus featuring mild reaction conditions, broad substrate scope, high functional group tolerance.

Language: Английский

Citations

17

Visible-light-driven Synthesis of Benzoxepine Derivatives from Aromatic Diazo Compounds DOI

Xiuyuan Duan,

Guojun Zheng

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134620 - 134620

Published: March 1, 2025

Language: Английский

Citations

0