Additive‐Free Generation of Cyanoalkyl Radicals via Photoinduced Single Electron Transfer from Dichalcogenides to Cycloketone Oxime Esters DOI
Xiaodi Su,

Bei‐Bei Zhang,

Qiang Liu

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(41)

Published: Sept. 9, 2022

Abstract We herein report an additive‐free alternative for the generation of cyanoalkyl radicals through photoinduced single electron transfer from dichalcogenides to cyclobutanone oxime esters, resulting in chalcogen‐containing nitriles. Experimental and DFT studies supported occurrence process between two components.

Language: Английский

Recent Advances in Light-Induced Selenylation DOI Creative Commons
Stefano Protti, Maurizio Fagnoni

ACS Organic & Inorganic Au, Journal Year: 2022, Volume and Issue: 2(6), P. 455 - 463

Published: Aug. 19, 2022

Selenium-containing organic molecules have recently found a plethora of applications, ranging from synthesis to pharmacology and material sciences. In view these concepts, the development mild, efficient, general protocols for formation C–Se bonds is desirable, light induced approaches are appealing ways. The aim this Review provide reader with most recent examples promoted selenylation processes.

Language: Английский

Citations

31
Organic Selenocyanates: Rapid Advancements and Applicationsin the Field of Organic Chemistry DOI
Pran Gopal Karmaker,

Feng Huo

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(8)

Published: June 15, 2022

Abstract The incorporation of the cyanato‐chalcogen group (OCN, SCN, and SeCN) has piqued interest many researchers in field modern organic synthetic chemistry. Methodologies for selenocyanation are far less advanced than those OCN SCN chemistry due to scarcity SeCN transfer reagents approaches. It also been discovered that selenocyanate precursor (SeCN) performs significantly better thiocyanate (SCN) terms pharmacological properties scaffolds. Recent years, new (nucleophilic, electrophilic, radical) techniques were introduced allowed creation selenocyanato uncomplicatedly under gentle reaction conditions, particularly transition metal catalysis photo‐/electro‐chemically influenced reactions, which seemingly unimaginable. In this review, we have categorized a variety using various types regents their applications last decades, focusing on multiple catalysts preparation selenocyanates derivatives.

Language: Английский

Citations

24
Dicarbofunctionalization of unactivated alkenes via organo-photoredox catalysis in water: access to cyanoalkylated fused quinazolinones DOI

Abuthayir Mohamathu Ghouse,

Srirama Murthy Akondi

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(26), P. 5351 - 5355

Published: Jan. 1, 2023

An organophotocatalyzed synthesis of polycyclic quinazolinones with a distal nitrile group is reported in the aqueous medium.

Language: Английский

Citations

9
Selective C–C bond cleavage of cycloketoximes via iminyl radicals and distal carbon radicals through photocatalysis DOI Creative Commons

Iram Kalsoom,

Muhammad Bılal, Aqsa Kanwal

et al.

Journal of Saudi Chemical Society, Journal Year: 2024, Volume and Issue: 28(3), P. 101848 - 101848

Published: March 22, 2024

The photocatalyzed cleavage of cycloketoximes is a promising approach for modifying their biological activity and designing prodrugs activated by light. Cycloketoximes containing cyclic ring structure that can hinder degradation modification in systems. Photocatalysis offers sustainable efficient method breaking down the using photocatalyst exposure to ultraviolet These reactions are initiated iminyl radicals, gain access distal-carbon through selective C–C cleavage. This process provides solution challenging task activities cycloketoximes. Moreover, it also be useful selectively removing protecting groups from organic molecules or cleaving specific chemical bonds, thereby facilitating synthesis.This review article covers synthetic uses highlights its ongoing research field photocatalysis.

Language: Английский

Citations

3
Organophotocatalytic Three‐Component Assembly of C4‐Cyanoalkylated Phthalazin‐1(2H)‐Ones DOI Open Access

Poornima Mishra,

Ruchir Kant,

Namrata Rastogi

et al.

Chemistry - An Asian Journal, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 14, 2025

Abstract The present work documents construction of C4‐cyanoalkylated phthalazinones under visible light‐mediated conditions. three‐component reaction involving aryl hydrazines, 2‐formylbenzoic acids and cyclobutanone oxime esters with organic dye Eosin Y as photocatalyst, features initial formation subsequent cyanoalkylation phthalazin‐1(2H)‐one in one pot. is notable for mild conditions, operational simplicity, wide substrate scope good yields the products. phthalazinone products were further converted into other valuable derivatives.

Language: Английский

Citations

0
Electrophilic Selenocyanogen Cyclization of Alkynes; Synthesis of Benzofurylselenocyanates, Benzothienylselenocyanates and Indolylselenocyanates DOI
Jia Wang,

Xiao‐Xiao Lu,

Xinqiang Tan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(13), P. 2235 - 2240

Published: May 7, 2022

Abstract A method to synthesize benzofurylselenocyanates, benzothienylselenocyanates and indolylselenocyanates via electrophilic selenocyanogen cyclization was established. This sequential process conducted under mild conditions in a short time. protocol successfully applied late‐stage functionalization of bioactive molecules. Notablely, the selenocyanate can be converted into other valuable Se‐containing compounds showed antitumor activity human hepatoma cells HepG2. magnified image

Language: Английский

Citations

13
Small-molecule organoselenocyanates: Recent developments toward synthesis, anticancer, and antioxidant activities DOI
Md. Badirujjaman, Nikita Pal, Krishna P. Bhabak

et al.

Current Opinion in Chemical Biology, Journal Year: 2023, Volume and Issue: 75, P. 102337 - 102337

Published: June 3, 2023

Language: Английский

Citations

8
A copper-catalyzed three-component reaction of alkenes, cycloketone oximes and DABCO·(SO2)2: Direct C(sp2)-H cyanoalkylsulfonylation DOI
Yating Liu,

Luoyu Wang,

Linghui Zeng

et al.

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 33(5), P. 2383 - 2386

Published: Nov. 10, 2021

Language: Английский

Citations

17
Lighting Up the Organochalcogen Synthesis: A Concise Update of Recent Photocatalyzed Approaches DOI Open Access
Ricardo H. Bartz,

Luiz H. Dapper,

Jean C. Kazmierczak

et al.

Catalysts, Journal Year: 2023, Volume and Issue: 13(3), P. 520 - 520

Published: March 3, 2023

This review describes the recent advances in photocatalyzed reactions to form new carbon–sulfur and carbon–selenium bonds. With a total of 136 references, which 81 articles are presented, authors introduce five sections an updated picture state art light-promoted synthesis organochalcogen compounds (from 2019 present). The sulfides by direct sulfenylation C–C π-bonds; sulfones; activation Csp2–N bond formation Csp2–S bonds; thiol ester, thioether thioacetal; organoselenium discussed, with detailed reaction conditions selected examples for each protocol.

Language: Английский

Citations

7
Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters DOI Creative Commons
Pu Chen, Huawen Huang,

Qi Tan

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(6), P. 2667 - 2667

Published: March 15, 2023

The synthetic strategies of oxime derivatives participating in radical-type reactions have been rapidly developed the last few decades. Among them, N–O bond cleavage esters leading to formation nitrogen-centered radicals triggers adjacent C–C produce carbon-centered free radicals, which has virtually used organic synthesis recent years. Herein, we summarized radical involving and through this special reaction form, including those from acyl ester cyclic ketoxime derivatives. These contents were systematically classified according different types. In review, after 2021 included, with emphasis on substrate scope mechanism.

Language: Английский

Citations

6