Divergent Reaction of Alkynes and TsCN: Synthesis of β-Sulfinyl Alkenylsulfones and (E)-Vinyl Sulfones DOI

Guiting Peng,

Xin Yu, Jiang Bai

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12159 - 12169

Published: Aug. 16, 2024

An efficient and high-selectivity approach for the divergent synthesis of β-sulfinyl alkenylsulfones (E)-vinyl sulfones from alkynes TsCN is described. A series disulfurized products were constructed under mild conditions in absence transition metals. This transformation featured excellent regio- stereoselectivity, good functional group compatibility, broad substrate scope. The copper(I)-catalyzed sulfonation with that affords to yields was also developed.

Language: Английский

Photoinduced Regioselective Sulfonylsulfination of Alkenes DOI
Helian Li, Yongxin Zhang, Xiuyuan Zou

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(5), P. 3664 - 3674

Published: Feb. 21, 2024

Regioselective 1,2-dichalcogenation of alkenes has attracted significant attention in modern organic synthetic chemistry. While there are a plethora methods to access alkene dichalcogenated architectures, sulfonylsulfination is extremely challenging due the inherent characteristics sulfur atom. Herein, multicomponent fragment coupling alkenes, sulfinates, and DABSO was developed construct densely functionalized sulfonylsulfinated products, which otherwise access, with broad substrate scope group tolerance under mild operationally simple conditions, using an inexpensive 100–1000 ppm photocatalyst. In addition, protocol applied late-stage functionalization complex molecules, obtained products were converted into diverse downstream transformations demonstrate their potential. Experimental theoretical mechanistic investigations suggest that these reactions proceed through sequential sulfonyl sulfinyl oxygen radical mutual radical–polar crossover coupling. This strategy provides previously inaccessible good-to-high regio- stereoselectivity, along opening up unexplored directions.

Language: Английский

Citations

17
Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization DOI
Chang‐Sheng Wang,

Yuan Xu,

Yiliang Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4972 - 5027

Published: Jan. 1, 2023

This review comprehensively summarizes the dichalcogenative functionalization of unsaturated compounds over past decade. The scopes, limitations and detailed reaction mechanisms are also discussed.

Language: Английский

Citations

20
Recent Advances in Electro- or Photochemical Driven Transformations via Cleavage of the C–N Bond of Quaternary Ammonium Salts DOI
X. KONG, Zhong‐Yan Cao, Xiaohui Chen

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2833 - 2842

Published: Jan. 26, 2023

Abstract Selective functionalization via cleavage of the C–N bond amines has proven to be challenging partly because its relatively high dissociation energy, even though are abundant and readily available. To meet this challenge, many new transformations based on pre-activation before have been developed. Among them, conversion into quaternary ammonium salts certain advantages, such as easy preparation from primary, secondary, or tertiary amines, well stable storage usage. Although transition metal catalysis frequently applied for developing oxidative addition salts, recent studies shown a dimension by using green electro- photochemical tools. In short review, advances in electro-, photo-, photoelectrochemical driven synthetic applications summarized discussed. 1 Introduction 2 Electrochemical Driven Transformations 3 Photochemical 4 Photoelectrochemical 5 Conclusion Outlook

Language: Английский

Citations

10
Photo-induced stereo- and regiospecific sulfonylation of C–C multiple bonds exploiting the dual reactivity of sulfonium iodate(i) species DOI
Aakanksha Gurawa, Nitin Kumar, Sudhir Kashyap

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4918 - 4926

Published: Jan. 1, 2023

The visible-light-directed stereospecific radical sulfonylation featuring the dual-reactivity of electrophilic reagent Me 3 SI(OAc) 2 is realized for vinyl-sulfonyl functionalization C( sp )-H and π bond in alkynes alkenes.

Language: Английский

Citations

10
Catalyst‐Free Visible Light‐Driven Hydrosulfonylation of Alkenes and Alkynes with Sulfonyl Chlorides in Water DOI

Xi‐Rui Xia,

Juan Du, Yuxing Zhang

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: unknown

Published: June 8, 2024

Abstract A convenient and sustainable method for synthesizing sulfonyl‐containing compounds through a catalyst‐free aqueous‐phase hydrosulfonylation of alkenes alkynes with sulfonyl chlorides under visible light irradiation is presented. Unactivated alkenes, electron‐deficient alkyl aryl can be hydrosulfonylated various at room temperature excellent yields geometric selectivities by using tris(trimethylsilyl)silane as hydrogen atom donor silyl radical precursor to activate chlorides. Mechanistic studies revealed that the photolysis in aqueous solution produce crucial success this reaction.

Language: Английский

Citations

3
Radical 1,3-Hydrosulfonylation of Vinyldiazo Compounds with Sulfinyl Sulfones DOI
Tian Jing, Yuan‐Li Ding,

Wanting Fu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 4, 2025

Sulfinyl sulfones, as high-valence sulfurization reagents, are widely used to assemble sulfur sources on carbon skeletons, such one-, two-, and four-carbon synthons, access organosulfur compounds. However, their reaction with three-carbon synthons has remained a mystery until now. We report here radical 1,3-hydrosulfonylation of vinyldiazo compounds sulfinyl sulfones. This not only represents the first example sulfones but also opens up application in monofunctionalization.

Language: Английский

Citations

0
Metal-free iodosulfonylation of alkynes to access (E)-β-iodovinyl sulfones in water DOI

Guiting Peng,

Fang Wei, Jiang Bai

et al.

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

Published: Jan. 1, 2025

We report a metal-free iodosulfonylation of alkynes in water at room temperature, which efficiently produces ( E )-β-iodovinyl sulfones good to excellent yields with high regio- and stereoselectivity.

Language: Английский

Citations

0
Photo-induced radical transformations of tosyl cyanide DOI
Ya Liu, Rui Li, Bing Yu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(2), P. 196 - 201

Published: Nov. 29, 2023

The recent advances in radical-involved transformations of tosyl cyanide (TsCN) are summarized.

Language: Английский

Citations

7
Divergent Reaction of Alkynes and TsCN: Synthesis of β-Sulfinyl Alkenylsulfones and (E)-Vinyl Sulfones DOI

Guiting Peng,

Xin Yu, Jiang Bai

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12159 - 12169

Published: Aug. 16, 2024

An efficient and high-selectivity approach for the divergent synthesis of β-sulfinyl alkenylsulfones (E)-vinyl sulfones from alkynes TsCN is described. A series disulfurized products were constructed under mild conditions in absence transition metals. This transformation featured excellent regio- stereoselectivity, good functional group compatibility, broad substrate scope. The copper(I)-catalyzed sulfonation with that affords to yields was also developed.

Language: Английский

Citations

2