Photoinduced Synthesis of Sulfonyl-Containing Phosphorothioates via a Three-Component Reaction DOI Creative Commons

Xianda Wu,

Minghong Chen,

Shuiyun Zheng

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(23), P. 7869 - 7869

Published: Nov. 30, 2023

Both sulfonyl and phosphorothioate are important privileged structural motifs which widely presented in pharmaceuticals agrochemicals. Herein, we describe an efficient approach to synthesizing sulfonyl-containing phosphorothioates by merging photoredox copper catalysis at room temperature. This protocol is compatible with a wide range of substrates can be applied the late-stage modification complex molecules. Control experiments conducted demonstrate generation radical transformation.

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
Self‐ or Acridinium‐Catalyzed Electrophotosynthesis of Thiocyanato Heterocycles from Activated Alkenes DOI

Kaixing Gong,

Yingchun Ma,

Ping Yu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2352 - 2362

Published: April 5, 2024

Abstract While the emergence of electrophotochemistry provides opportunities, such a chemistry at this stage suffers from limited reaction types and high photocatalyst loadings. A self‐catalyzed electrophotosynthesis as well one with low loading is presented. These external‐oxidant‐free cyclizations are enabling applicable to range activated alkenes, affording diverse array thiocyanato heterocycles including 4‐pyrrolin‐2‐ones, isoquinoline‐1,3‐diones, indolo[2,1‐ ]isoquinolin‐6(5 H )‐ones, benzoimidazo[2,1‐ )‐ones indolin‐2‐ones, protocols amenable late‐stage diversification complex molecular architectures gram‐scale syntheses. Sunlight could serve light source, be conducted in an all‐solar‐driven mode using commercially available photovoltaic panel produce electricity.

Language: Английский

Citations

10
Multicomponent Reactions Based on SO2 Surrogates: Recent Advances DOI
Gang Chen, Zhong Lian

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(25)

Published: April 25, 2023

Abstract Compounds containing sulfonyl‐derived functional groups have received intensive attention owing to their widespread applications in life science, pharmaceuticals and materials science. To access this type of compounds, the multi‐component sulfonylation reactions relying on sulfur dioxide (SO 2 ) insertion strategy emerged as novel attractive approaches past decade. The utilization SO surrogates for multicomponent (MCRs) improved reaction flexibility step economy. Moreover, some advances been achieved challenging but practical asymmetric MCRs construction high value‐added chiral sulfones. This review aims summarize progress made involving from 2019 2022, point out potentials challenges field.

Language: Английский

Citations

23
Copper-Catalyzed 1,4-Trifluoromethylthio-Arylsulfonylation of 1,3-Enynes via the Insertion of Sulfur Dioxide DOI

Hongzhuo Song,

Xuemei Zhang, Gang Chen

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(31), P. 5916 - 5921

Published: July 27, 2023

A copper-catalyzed trifluoromethylthio-arylsulfonylation between 1,3-enynes, AgSCF3, aryldiazonium tetrafluoroborates, and SO2 (from SOgen) is presented, which could introduce sulfone, SCF3, allene moieties into one molecule simultaneously. This strategy features mild reaction conditions, good substrate compatibility, excellent regioselectivity. The products obtained have the potential for further conversion other valuable compounds. Initial investigations mechanism suggest that it may proceed via a radical pathway. Notably, SOgen was proven as uniquely effective surrogate in this transformation.

Language: Английский

Citations

17
Access to chiral β-amino sulfones from acrylamides and sulfur dioxide by iron catalysis DOI
Liping Luo, Xuemei Zhang,

Chunxi Huang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1678 - 1684

Published: Jan. 1, 2024

This method allows for the enantioselective synthesis of β-azide sulfones via iron-catalyzed vicinal azide-sulfonylation acrylamides. It makes first instance achieving asymmetric construction through iron catalysis with SO 2 insertion.

Language: Английский

Citations

5
Introducing Alkyl Selenocyanates as Bifunctional Reagents in Photoredox Catalysis: Divergent Access to Ambident Isomers of −SeCN DOI

Shyamal Pramanik,

Avik Kr Das,

Saradindu Debnath

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(40), P. 8447 - 8452

Published: Aug. 22, 2024

Owing to their diverse biological activities and versatility as synthetic precursors, organoselonocyanes categorize themselves vital compounds. However, a limited reagent pool restricts utility. In the present work, alkyl selenocyanates are hereby established new bifunctional reagents for simultaneous transfer of an group in addition −SeCN. These reagents, when merged with photocatalysis, provide key accessing organoselenocyanates from feedstock olefins efficient atom-economic fashion. A route analogous isoselenocyanate isomers facilitated by Lewis acid catalysis is also reported, presenting divergent strategy both ambident −SeCN manner.

Language: Английский

Citations

4
Visible-Light-Mediated Divergent and Regioselective Vicinal Difunctionalization of Styrenes with Arylazo Sulfones DOI
Lorenzo Di Terlizzi, Luca Nicchio, Camilla Callegari

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(50), P. 9047 - 9052

Published: Dec. 12, 2023

Activated by visible light, arylazo sulfones can serve as multifaceted reactants and are employed in diazenylation, sulfonylation, arylation reactions under (photo)catalyst-free conditions. Such versatile reactivity enabled us to develop an operationally simple, regioselective, tunable difunctionalization of styrenes with produce α-sulfonyl arylhydrazones 1,2-alkoxyarylated products moderate excellent yields. Furthermore, such difunctionalized have been exploited key building blocks for the synthesis various heterocycles.

Language: Английский

Citations

9
Alkylsulfonylation of alkenes involving copper carbene coupling: access to alkyl–alkyl sulfones DOI

Chuan‐Chong Peng,

Fang Long,

Rui Feng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1975 - 1981

Published: Jan. 1, 2024

A novel alkyl radical-initiated alkylsulfonylation of alkenes involving copper carbene coupling is developed for the synthesis various alkyl–alkyl sulfones by employing potassium metabisulphite (K 2 S O 5 ) as a connector.

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
Inverse conjugate additions of acrylic amides and esters with F/Cl/O/N-nucleophiles and CF 3 + reagents DOI Creative Commons

Xiukun Liu,

Yuan Kou,

Hao Wu

et al.

Science Advances, Journal Year: 2025, Volume and Issue: 11(7)

Published: Feb. 12, 2025

The conjugate additions of nucleophiles to acceptors are among the most powerful hetero-carbon bond formation reactions. addition normally occurs via a β-nucleophilic addition, resulting in stabilized α-carbanion intermediate that can be subsequently quenched by electrophiles or protons. Nevertheless, inverse involving an α-specific nucleophilic remains less explored because electronic mismatch. In this research, we disclosed including Py·HF, TBACl, HOR, H 2 O, 18 RCO H, and pyrazole concurrent with trifluoromethylation. This umpolung inversely regioselective enabled visible light–induced redox photocatalysis, occurred unusual α-nucleophilic other than normal efficiently generate diverse α-functionalized CF 3 -containing amides/esters. broad substrate scope, excellent functional-group tolerance, versatile late-stage derivatizations as well biologically functionally important products demonstrated potential applications protocol materials, agrochemicals, pharmaceutical chemistry.

Language: Английский

Citations

0