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 advances in the application of alkynes in multicomponent reactions DOI Creative Commons
Seyedmohammad Hosseininezhad, Ali Ramazani

RSC Advances, Journal Year: 2024, Volume and Issue: 14(1), P. 278 - 352

Published: Jan. 1, 2024

The reactions and mechanisms of alkynes that are involved in multi-component through C–C C–H positions investigated.

Language: Английский

Citations

12

Versatile electrooxidative amino- and oxyselenation of alkenes DOI
R. Wang,

Nana Zhang,

Yonghong Zhang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(10), P. 3925 - 3930

Published: Jan. 1, 2023

We herein describe a methodology for the production of organoselenium compounds by electrocatalytic difunctionalisation alkenes.

Language: Английский

Citations

20

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

Oxidative Three-Component Selenofunctionalization of Alkenes: Convenient Access to Vicinally Functionalized Selenides DOI
Yun‐Qian Zhang,

You‐Qin Jiang,

Yong‐Hao Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7431 - 7447

Published: May 23, 2023

Three-component selenofunctionalization processes of olefins, diselenides and sulfonamides, water, alcohols, or acids utilizing 1-fluoropyridinium triflate (FP-OTf) as a reaction promoter are reported. Under the optimal conditions, broad range vicinally functionalized selenide derivatives was accessible with high yields excellent functional group compatibilities. Mechanistic studies revealed that FP-OTf played key role in this process.

Language: Английский

Citations

15

Electrochemical Synthesis of Organoselenium Compounds: A Graphical Review DOI Creative Commons
Zhixiong Ruan,

Balati Hasimujiang

SynOpen, Journal Year: 2023, Volume and Issue: 07(04), P. 511 - 520

Published: Oct. 1, 2023

Abstract Electrochemical synthesis, due to its environmentally benign, sustainable, and practical nature, has become an appealing powerful substitute for traditional methods oxidizing reducing organic compounds. Thus, numerous valuable changes have been established in the field of synthesis through utilization electrochemistry. Among these electrochemical transformations, formation C–Se bonds stands out as exceptionally noteworthy reaction type. In this graphical review, we present a succinct summary progress utilizing strategies synthesizing organoselenium

Language: Английский

Citations

12

Intermolecular 1,2-Difunctionalization of Terminal Alkynes to Access Trisubstituted Alkenes via Copper/Photoredox Dual Catalysis DOI
Fei Tang, Yi‐Si Feng, Zhi-Fei Cheng

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(21), P. 3916 - 3921

Published: May 22, 2023

We report a copper metallaphotocatalytic 1,2-difunctionalization of terminal alkynes with N-hydroxyphthalimide (NHP) esters and readily available silyl reagents (TMSCN TMSNCS) to access stereodefined trisubstituted alkenes, including (E)-alkenyl nitriles thiocyanates. The reaction proceeds excellent anti-stereoselectivity demonstrates broad compatibility wide range NHP as alkyl radical precursors. Experimental computational studies have been performed gain insight into the mechanism.

Language: Английский

Citations

9

Electrochemical Synthesis of α-Thiocyanated/Methoxylated Ketones Using Enol Acetates DOI
Peng Zhang, Junwei Ma, Xuan Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(23), P. 16122 - 16131

Published: Nov. 14, 2023

We have developed the synthesis of α-substituted ketone compounds with enol acetates in an electrochemical way. By using cheap NH4SCN and MeOH as radical sources, a series valuable α-thiocyanates/methoxy ketones were synthesized under mild electrolysis conditions acceptable yields diverse functional group compatibility. Additionally, scale-up experiment synthetic transformations reveal potential applications organic synthesis.

Language: Английский

Citations

9

A sustainable approach for the bis-selenylation of alkynes: Design, synthesis and mechanistic studies DOI
Lucas Martins Correa Böhs,

Calebe Hebrom Livistom Silva,

Natália Emanuele Biolosor Kuntz

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155504 - 155504

Published: Feb. 1, 2025

Language: Английский

Citations

0

Photocatalyzed Annulation‐Biselenylation of Enynone with Diarylselenides toward Biselenium‐Substituted 1‐Indanones under Metal‐ and Photosensitizer‐Free Conditions DOI
Hang‐Dong Zuo,

Huafeng Yan,

Yuting Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 17, 2025

Comprehensive Summary A practical photocatalytic annulation‐biselenylation strategy has been developed for the efficient synthesis of biselenium‐substituted 1‐indanones (38 examples in total) with generally good yields (up to 95%) and excellent stereoselectivity (>19 : 1 Z / E ratio) by employing enynones diaryl selenides as starting materials under photosensitizer‐free conditions. The reaction mechanism involves a cascade process comprising homolytic cleavage, radical addition, 5‐ exo ‐ dig cyclization, capture, enabling sequential formation multiple bonds, such C(sp 3 )‐Se, )‐C(sp 2 ), )‐Se rapidly construct molecular complexity. Notably, this approach demonstrates wide substrate compatibility tolerability towards various functional groups. It is further characterized its remarkable efficiency creating chemical bonds achieving high atomic utilization 100%.

Language: Английский

Citations

0