Recent Developments in C‐S, C‐Se Bond Formation via Three‐Component Reactions of Alkynes DOI Open Access
Zhan‐Yong Wang, Guipeng Feng, Xiaoying Jiang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(46)

Published: Aug. 28, 2024

Abstract Alkynes are valuable building blocks in organic synthesis. They can undergo three‐component difunctionalization to create sulfur or selenium‐containing compounds. Three‐component reactions of alkynes atom economic, practical and regioselective. This review will disscuss decade developments, including C−S C−Se bond formation via thiolation, sulfonylation selenylation. Recent developments be mainly categorized into three types. (1) Radical C−S/S−Se is a hot topic. Reactions initiated by S/Se radicals other exhibit two types selectivities. Photochemical electrochemical under eco‐friendly conditions have been increasingly reported. (2) Some transformations involve electrophilic three‐membered ring intermediates. Thiiraniums, seleniraniums, iodoniums among the most prevalent species. ring‐opening various nucleophiles participate tandem reactions. (3) Metal‐catalyzed reactions, classic category, also discussed text. In following section, we provide an overview based on mechanisms substrates. The roles added reagents discussed.

Language: Английский

Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation DOI
Jianchao Liu, Jie‐Ping Wan, Yunyun Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(2), P. 597 - 630

Published: Nov. 23, 2023

This review highlights the recent progress in electrochemical difunctionalization of alkenes and alkynes involving C–S/Se bond formation to access organochalcogen frameworks.

Language: Английский

Citations

31

Regio- and Stereoselective Synthesis of 3-Selenylazaflavanones and 3-Selenylflavanones via Electrochemically Facilitated Selenylation Cascade DOI

Shaogao Zeng,

Yong Zeng, Hui Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 4074 - 4084

Published: Feb. 23, 2024

Herein, an oxidant- and metal-free electrochemical selenylation reaction of chalcones with diselenides for the synthesis 3-selenylazaflavanones 3-selenylflavanones at room temperature was reported. The method proceeded under mild conditions, exhibited a broad substrate scope, provided selenylated products in moderate to excellent yields high regio- stereoselectivity. could also be readily scaled up efficiency. Detailed mechanistic studies through control experiments disclosed that selenium-based radical might participate this transformation.

Language: Английский

Citations

10

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

1

Electrochemical selenofunctionalization of unactivated alkenes: access to β-hydroxy-selenides DOI
Anil Balajirao Dapkekar, Gedu Satyanarayana

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(9), P. 1775 - 1781

Published: Jan. 1, 2024

This work demonstrates the electrochemical construction of 2-methyl-1-aryloxy-3-(arylselanyl)propan-2-ol/2-hydroxy-2-methyl-3-(arylselanyl)propyl 2-(2-hydroxy-2-methyl-3-(arylselanyl)propoxy)benzoate starting from aryl allyl ethers/allyl benzoates and diaryl diselenides under additive-free conditions. environmentally friendly method was achieved through constant current electrolysis in an undivided cell setup acid, oxidant, or catalyst-free Additionally, this technique enabled synthesis a variety β-hydroxy selenides including late-stage functionalization drug derivatives good to exceptional yields across various substrates mild reaction

Language: Английский

Citations

8

Visible-light induced selenocyclization of 2-ethynylanilines under ambient conditions: simple FeBr3 as a dual-functional catalyst DOI
Binbin Huang,

Xinye Tang,

Jiawei Yuan

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(30), P. 6198 - 6204

Published: Jan. 1, 2024

Reported herein is a visible-light induced selenocyclization of 2-ethynylanilines under ambient conditions, with simple FeBr 3 as dual-functional catalyst.

Language: Английский

Citations

7

An electrocatalytic mono-functionalization of alkenes towards alkenyl selenium sulfonates DOI

Zhiheng Zhao,

Hongyan Yan,

Lijun Gu

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

In this study, a straightforward and environmentally benign electrochemical mono-functionalization of alkenes has been established for the synthesis alkenyl selenium sulfonates using elemental as source.

Language: Английский

Citations

1

Electrophotocatalysis Versus Indirect Electrolysis: Electrochemical Selenocyclization of 3‐Aza‐1,5‐dienes Facilitated by Energy Transfer, Direct Photolysis or N‐Hydroxyphthalimide DOI

Dongyin Wang,

Li Zeng, Jifu Shi

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(36)

Published: April 23, 2024

Three hybrid electrochemical protocols, which involve the energy transfer, direct photolysis and N-hydroxyphthalimide catalyst, respectively, are presented for selenylation/cyclization of fragile substrates 3-aza-1,5-dienes with diorganyl diselenides to afford 3-selenomethyl-4-pyrrolin-2-ones. The two electrophotocatalytic reactions indirect electrolysis one both regioselective external-oxidant- transition-metal-free, associated a broad substrate scope high Se-economy, all three methods amenable gram-scale syntheses, late-stage functionalizations, sunlight-induced experiments all-solar-driven syntheses.

Language: Английский

Citations

6

Lewis Base Catalyzed Selenofunctionalization of Alkynes with Acid‐Controlled Divergent Chemoselectivity DOI
Ling‐Ling Chen,

Ren‐Fei Cao,

Hua Ke

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(14), P. 1623 - 1629

Published: March 15, 2024

Comprehensive Summary Lewis base catalyzed and Brønsted acid controlled chemodivergent electrophilic selenofunctionalizations of alkynes were developed for the first time. Various selenium‐containing tetrasubstituted alkenes readily obtained in moderate to excellent yields with complete E / Z selectivities. As substrates 1‐ethynyl naphthol derivatives, linear produced via intermolecular oxygen nucleophilic attack absence additive; contrast, cyclic generated through intramolecular carbon capture addition acid.

Language: Английский

Citations

5

Electricity-driven, oxidative C–H selenylative and tellurylative annulation of N-(2-alkynyl)anilines: sustainable synthesis of 3-selanyl/tellanylquinolines DOI Creative Commons

Ainala Naresh,

H. Sai Keerthana,

Nilanjana Mukherjee

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(55), P. 7057 - 7060

Published: Jan. 1, 2024

A metal- and oxidant-free, electricity-driven C–H selenylative tellurylative annulation of N -(2-alkynyl)anilines with diorganyl dichalcogenides is developed to access 3-chalcogenylquinolines.

Language: Английский

Citations

5

Recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of C(sp2)–H and C(sp3)–H bonds DOI
Chang‐Sheng Wang, Yuan Xu, Shaopeng Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(4), P. 645 - 681

Published: Dec. 23, 2023

Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic intermediates. Direct chalcogenation of C-H bonds has evolved as a step- atom-economical method for the synthesis chalcogen-bearing compounds. Nevertheless, direct severely lags behind C-C, C-N C-O bond formations. Moreover, compared with monochalcogenation, reports selective mono-/dichalcogenation exclusive dichalcogenation relatively scarce. The past decade witnessed significant advancements various C(sp

Language: Английский

Citations

10