Catalytic Enantioselective Electrophilic Difunctionalization of Unsaturated Sulfones DOI

Xinru Xu,

Tian Qin, Nan Huang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(21), P. 4514 - 4519

Published: May 17, 2024

An efficient protocol of enantioselective thiolative azidation sulfone-tethered alkenes via a chiral chalcogenide catalyzed electrophilic reaction is disclosed. A series enantioenriched sulfones bearing remote stereogenic centers was achieved with good yields and high enantioselectivities linear unsaturated cyclic sulfones. Mechanistic studies revealed the importance sulfone group in improvement reactivity enantioselectivity reaction.

Language: Английский

Enantioselective sulfonylation using sodium hydrogen sulfite, 4-substituted Hantzsch esters and 1-(arylethynyl)naphthalen-2-ols DOI
Xinhua Wang, Qiuping Ding, Chenxi Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(1), P. 92 - 98

Published: Nov. 11, 2022

Synthesis of sulfonyl-containing axially chiral styrenes through a catalytic asymmetric reaction 4-substituted Hantzsch esters, sodium hydrogen sulfite and 1-(arylethynyl)naphthalen-2-ols is reported.

Language: Английский

Citations

19

Visible-Light-Induced Synthesis of Alkylsulfonated Isoquinolinones from 2-Aryl Indoles/Benzimidazoles through Insertion of Sulfur Dioxide DOI

Xin‐Qian Liu,

Yang Guo,

Wen-Qin Yu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 9293 - 9305

Published: June 7, 2023

A visible-light-induced three-component reaction of 2-aryl indoles/benzimidazoles, Hantzsch esters, and sodium pyrosulfite through a radical cascade cyclization process with the insertion sulfur dioxide is described. It provides novel powerful way for synthesis alkylsulfonated isoquinolinones. esters Na2S2O5 are employed as alkyl precursors SO2 surrogate, respectively. This transformation exhibits good functional group tolerance substrate applicability under mild conditions.

Language: Английский

Citations

12

A palladium-catalyzed cross-electrophile coupling reaction involving sulfur dioxide for the direct synthesis of diversely functionalized sulfones DOI
Baojian Xiong, Jinyu Zhang, Ting Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(14), P. 3567 - 3576

Published: Jan. 1, 2023

A palladium catalyzed multi-component cross-electrophile coupling involving sulfur dioxide is presented here. This protocol features mild reaction conditions, wide substrate scope, good functional group tolerance and excellent regioselectivity.

Language: Английский

Citations

11

SO2-Insertion induced enantioselective oxysulfonylation to access β-chiral sulfones with quaternary carbon stereocenters DOI
Jun Zhang,

Xuefeng Wang,

Peiqi Wang

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 67(3), P. 908 - 913

Published: Dec. 5, 2023

Language: Английский

Citations

11

Recent advances in the palladium-catalyzed sulfonylation via SO2 insertion DOI
Yujiao Zhang,

Meng-Ling Li,

Haixia Hu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(29), P. 5868 - 5885

Published: Jan. 1, 2024

The importance of sulfonyl-group-containing compounds, such as sulfonamides, sulfones, sulfinate esters, and sulfonyl fluorides, in pharmaceuticals, bioactive molecules, natural products cannot be overstated. new development palladium-catalyzed sulfonylation

Language: Английский

Citations

4

Generation of perthiyl radicals for the synthesis of unsymmetric disulfides DOI Creative Commons

Fei Zhou,

X. He, Mi Zhou

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 2, 2025

Unsymmetric disulfides are prevalent in natural products and essential medicinal chemistry materials science, but their robust synthesis poses significant challenges. In this paper, we report an expeditous transition-metal-free methodology for synthesizing unsymmetric through the addition of perthiyl radicals to alkenes. This study marks use generating by reacting SO2 with unactivated alkyl (pseudo)halides (Cl/Br/I/OTs). Various primary, secondary tertiary substituted different functional groups successfully function as suitable reactants. The formation involvement reaction process verified mechanistic studies DFT calculations. Overall, method leverages readily available electrophiles alkenes alongside a single setup efficiently form both carbon-sulfur sulfur-sulfur bonds simultaneously. Here, authors novel transition-metalfree

Language: Английский

Citations

0

Recent Progress in C–S Bond Formation via Electron Donor-Acceptor Photoactivation DOI
Sichang Wang, Liting Wang, Jin Cui

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review summarizes recent progress in EDA complex-promoted C–S bond formation using various sulfur-containing substrates under mild conditions via visible light irradiation.

Language: Английский

Citations

0

The application and development of cyanating reagents in asymmetric cyanation reactions DOI
Ruirui Hua, Chukai Shao, Fu‐Xue Chen

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155549 - 155549

Published: March 1, 2025

Language: Английский

Citations

0

Palladium-catalyzed domino cyclization/direct functionalization involving the insertion of SO2 DOI
Xinwei Zhang,

Yaoyao Lu,

Shuoshuo Zhang

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(12), P. 5101 - 5106

Published: Jan. 1, 2024

A reductive cross-coupling strategy for the synthesis of sulfone-containing oxindoles was presented. Moreover, using amines instead alkyl bromides, a palladium-catalyzed domino cyclization/aminosulfonylation also established.

Language: Английский

Citations

3

Access to chiral sulfones with an all-carbon quaternary stereocenter from sulfur dioxide DOI

Chunxi Huang,

Xuemei Zhang, Liping Luo

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4275 - 4283

Published: Jan. 1, 2024

A copper-catalyzed enantioselective four-component reaction via the insertion of sulfur dioxide toward synthesis chiral sulfones bearing an all-carbon quaternary stereocenter at β position is reported.

Language: Английский

Citations

3