Zn(OTf)2-catalyzed intra- and intermolecular selenofunctionalization of alkenes under mild conditions DOI Creative Commons

Cong Qi,

Zhaogong Lu,

Yuyang Gu

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(32), P. 23147 - 23151

Published: Jan. 1, 2024

Zn(OTf)2-catalyzed intra- and intermolecular selenofunctionalization of alkenes was achieved with electrophilic N-phenylselenophthalimide. This method provides straightforward efficient access to various seleno-substituted heterocycles vicinal Se heteroatom-disubstituted molecules under mild conditions. reaction is compatible substrates/functional groups, preliminary studies on the mechanistic were also conducted.

Language: Английский

Recent progress in the electrochemical selenofunctionalization of alkenes and alkynes DOI
Pei Qu,

You‐Qin Jiang,

Yong‐Hao Wang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(19), P. 7485 - 7507

Published: Jan. 1, 2023

The recent advances on the electrochemical selenofunctionalization of unsaturated C–C bonds were comprehensively summarized in this review.

Language: Английский

Citations

32
Recent progress in the organoselenium-catalyzed difunctionalization of alkenes DOI
Pei Qu, Gong‐Qing Liu

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

Published: Jan. 1, 2025

Selenium-based catalysts have recently been utilized to facilitate a variety of new organic transformations, owing their intrinsic advantages, including low cost, toxicity, stability in both air and water, strong compatibility with diverse functional groups. The difunctionalization alkenes-the process incorporating two groups onto carbon-carbon double bond-has garnered particular interest within the chemical community its significant applications synthesis. Recently, organoselenium-catalyzed alkenes has emerged as an ideal powerful route obtain high-value vicinal difunctionalized molecules. This review emphasizes recent advancements this rapidly evolving field, focusing on scope, limitations, mechanisms various reactions.

Language: Английский

Citations

0
Organoselenium Catalyzed Electrochemical Cascade Cyclization: An Access to Naphthofuran‐2‐carboxaldehyde DOI
Neha Dagar, Swati Singh, Sudipta Raha Roy

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(11), P. 2544 - 2550

Published: April 5, 2024

Abstract We have developed an approach for the construction of naphthofuran‐2‐carboxaldehyde derivatives utilizing synergy electrochemical oxidation and organo‐selenium catalysis at room temperature. The compatibility various functional groups scalability this protocol demonstrate practicality strategy. synthetic utility strategy is furthermore demonstrated by synthesizing diversified molecules through downstream transformations.

Language: Английский

Citations

3
Photoinduced, trans‐Diastreoselective Oxyselenenylation of Allylic Alcohols to Form Selenylated Cyclic Boronic Esters DOI
Pei Qu,

You‐Qin Jiang,

Hongmei Wu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(14), P. 3160 - 3165

Published: May 25, 2024

Abstract A visible‐light‐induced method was developed to synthesize selenylated cyclic boronic esters through intermolecular oxyselenenylation. This can be performed under additive‐free and photocatalyst‐free conditions generates potentially pharmaceutically useful heterocycles. plausible reaction mechanism proposed based on several control experiments previous reports.

Language: Английский

Citations

2
Photoinduced Intermolecular Hydroamination and Hydroetherification of Electron‐Rich Alkenes With Low Catalyst Loadings DOI

You‐Qin Jiang,

Pei Qu,

Yong‐Hao Wang

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: 17(22)

Published: July 24, 2024

Abstract A photochemical method based on visible‐light irradiation (blue LEDs/sunlight) has been developed for the intermolecular hydroamination and hydroetherification of electron‐rich alkenes. This is compatible with a wide range azoles alkenes, such as vinyl ethers, sulfides enamides, performed low concentrations photocatalyst (1000 ppm). Comprehensive mechanistic studies indicate that this process initiated by formation an active radical cation intermediate through single electron oxidation azole, which mediated excited Acr‐Mes + BF 4 − .

Language: Английский

Citations

2
N‐Halosuccinimide‐CeCl3 Transient Charge‐Transfer Complexes as Semi Heterogeneous Photocatalyst in Cyclization of N‐Propargylamides DOI
Sathi Sahoo, Tarun Kumar Dinda, Prasenjit Mal

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(57)

Published: Aug. 1, 2024

In this work, we used photoinert anhydrous cerium(III) chloride, to form a transient charge-transfer (CT) complex with NXS (N-bromosuccinimide or NBS and N-iodosuccinimide NIS) in acetonitrile. These CT complexes acted as semi-heterogeneous photocatalyst. allowed the Ce(III) ions absorb light, turning them into strong electron donors that transferred electrons NXS. This created halide radicals from radical anions, helping turn N-propargylamides oxazole aldehydes. Experiments DMPO spin-trapping showed radical-based mechanism followed single transfer (SET) pathway. Notably, CeCl

Language: Английский

Citations

1
Synthesis of Oxazoles Containing CF3-Substituted Alcohol Unit via Tandem Cycloisomerization/Hydroxyalkylation from N-Propargylamides with Trifluoropyruvates DOI Creative Commons
Juanjuan Gao,

Longhui Wu,

Shuqin Yu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(24), P. 5848 - 5848

Published: Dec. 11, 2024

Oxazoles are important five-membered heterocycles that contain both nitrogen and oxygen atoms. Due to their wide range of biological activities, many oxazoles demonstrate potential for extensive application in various fields, including medicinal chemistry. Trifluoromethyl carbinol, an pharmacophore, contains trifluoromethyl hydroxyl groups is common molecules with activities. Constructing a carbinol unit undoubtedly valuable expanding the chemical space drug discovery. In this study, simple efficient method was developed synthesis containing CF3-substituted alcohol via tandem cycloisomerization/hydroxyalkylation N-propargylamides trifluoropyruvates through rational Lewis acid catalytic mechanism. This Zn(OTf)2-catalyzed synthetic protocol operationally provides series moderate good yields. The demonstrates broad substrate scope, high functional group tolerance, atom economy can achieve gram-level reactions, indicating strong possibility its practical application.

Language: Английский

Citations

1
Zn(OTf)2-catalyzed intra- and intermolecular selenofunctionalization of alkenes under mild conditions DOI Creative Commons

Cong Qi,

Zhaogong Lu,

Yuyang Gu

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(32), P. 23147 - 23151

Published: Jan. 1, 2024

Zn(OTf)2-catalyzed intra- and intermolecular selenofunctionalization of alkenes was achieved with electrophilic N-phenylselenophthalimide. This method provides straightforward efficient access to various seleno-substituted heterocycles vicinal Se heteroatom-disubstituted molecules under mild conditions. reaction is compatible substrates/functional groups, preliminary studies on the mechanistic were also conducted.

Language: Английский

Citations

0