Mechanochemical Solvent‐Free One‐Pot Synthesis of Poly‐Functionalized 5‐(Arylselanyl)‐1H‐1,2,3‐triazoles Through a Copper(I)‐Catalyzed Click Reaction DOI
Pintu Karmakar, Indrajit Karmakar, Debojyoti Mukherjee

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(63)

Published: Sept. 4, 2023

A mechanochemistry-driven practical and efficient synthetic protocol for accessing diverse series of biologically relevant poly-functionalized 5-(arylselanyl)-1H-1,2,3-triazoles through copper(I)-catalyzed click reaction between aryl/heteroaryl acetylenes, diaryl diselenides, benzyl bromides, sodium azide has been accomplished under high-speed ball-milling. Advantages this method include operational simplicity, avoidance using solvent external heating, one-pot synthesis, short time in minutes, good to excellent yields, broad substrate scope, gram-scale applications. Furthermore, synthesized organoselenium compounds were synthetically diversified promising selenones.

Language: Английский

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges DOI
I. P. Beletskaya, Valentine P. Ananikov

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(21), P. 16110 - 16293

Published: Sept. 16, 2022

In the present review, we discuss recent progress in field of C–Z bond formation reactions (Z = S, Se, Te) catalyzed by transition metals. Two complementary methodologies are considered─catalytic cross-coupling and catalytic addition reactions. The development advanced systems is aimed at improved catalyst efficiency, reduced loading, better cost environmental concerns, higher selectivity yields. important rise research efforts sustainability green chemistry areas critically assessed. paramount role mechanistic studies a new generation addressed, key achievements, problems, challenges summarized for this field.

Language: Английский

Citations

201
Decoding Directing Groups and Their Pivotal Role in C−H Activation DOI
Karunanidhi Murali, Luana A. Machado, Renato L. Carvalho

et al.

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(49), P. 12453 - 12508

Published: May 26, 2021

Synthetic organic chemistry has witnessed a plethora of functionalization and defunctionalization strategies. In this regard, C-H been at the forefront due to multifarious applications in development simple complex molecular architectures holds brilliant prospect drug discovery. Despite explored tremendously by chemists, strategy still enjoys employment novel metal catalysts as well metal-free ligands. Moreover, switch photo- electrochemistry widened our understanding alternative pathways via which reaction can proceed these strategies have garnered prominence when applied activation. chemists foraging for new directing groups templates selective activation bonds from myriad carbon-hydrogen aromatic aliphatic systems. As matter fact, varying groups, scientists found answer challenge distal bond remained an obstacle very long time. These frequently harnessed selectively activating natural products, drugs, macromolecules decorated with multiple bonds. This itself was before commencement field site other than targeted could modify hamper biological activity pharmacophore. Total synthesis pharmacophore often faces difficulty superfluous steps towards functionalization. solved late-stage simply harnessing green conditions seen light past few decades rising concern about environmental issues. Therefore, or usage non-toxic metals recently showcased number elegant works. Also, research across world are developing rational group free non-directed protocols that just guided review encapsulates works pertinent discusses science devoted it fundamental level. gives readers broad how work, execution various catalysts, groups. not only helps budding scientist his/her but also matured mind searching out A detailed picture its progress time portrayed lucid scientific language motive inculcate educate minds beautiful overview most relevant significant era. The unique trait is description classification their utility over wide substrate scope. allows experimental chemist understand applicability domain employ any substrate.

Language: Английский

Citations

97
Chelation-assisted transition metal-catalysed C–H chalcogenylations DOI Open Access
Wenbo Ma, Nikolaos Kaplaneris,

Xinyue Fang

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(8), P. 1022 - 1060

Published: Jan. 1, 2020

This review summarizes recent advances in C–S and C–Se formationsviatransition metal-catalyzed C–H functionalization utilizing directing groups to control the site-selectivity.

Language: Английский

Citations

80
Electrochemical Regioselective C(sp2)–H Selenylation and Sulfenylation of Substituted 2-Amino-1,4-naphthoquinones DOI
Pintu Karmakar, Indrajit Karmakar, D. R. PAL

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(2), P. 1049 - 1060

Published: Jan. 4, 2023

A straightforward and efficient electrochemical method for regioselective C(sp2)-H selenylation sulfenylation of substituted 2-amino-1,4-naphthoquinones has been unearthed. This oxidative cross-coupling reaction avoids using transition metal catalysts, oxidants, high temperatures. The other notable advantages this protocol are the tolerance diverse functional groups, mild conditions at ambient temperature, energy efficiency, good to excellent yields, short times (in minutes), gram-scale applicability, eco-friendliness.

Language: Английский

Citations

22
The crucial role of silver(i)-salts as additives in C–H activation reactions: overall analysis of their versatility and applicability DOI Creative Commons
Renato L. Carvalho, Emilay B. T. Diogo, Simon L. Homölle

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(18), P. 6359 - 6378

Published: Jan. 1, 2023

This review discusses the important role of silver( i ) salts as additives in transition-metal catalyzed C–H activation, and depicts discussion about current shift towards Ag-free procedures, plausible sustainable alternatives.

Language: Английский

Citations

21
Electrochemical Selenylation of Sulfoxonium Ylides for the Synthesis of gem-Diselenides as Antimicrobials against Fungi DOI
Zhongnan Xu,

Jiwen Yao,

Kaihui Zhong

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5572 - 5585

Published: April 21, 2023

Organoselenium compounds are important scaffolds in pharmaceutical molecules. Herein, we report metal-free, electrochemical, highly chemo- and regioselective synthesis of gem-diselenides through the coupling α-keto sulfoxonium ylides with diselenides. The versatility electrochemical manifold enabled selenylation ample scope broad functional group tolerance, as well setting stage for modification complex bioactive Detailed mechanistic studies revealed that key C-Se bond was constructed using n-Bu4NI an electrolyte catalyst electrosynthetic protocol. Finally, desired showed excellent antimicrobial activity against Candida albicans, which can be identified lead further exploration.

Language: Английский

Citations

19
Palladium-Catalyzed Direct Ortho-C–H Selenylation of Benzaldehydes Using Benzidine as a Transient Directing Group DOI

Huihao Qiao,

Bing Sun, Qinqin Yu

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(17), P. 6914 - 6918

Published: Aug. 26, 2019

Benzidine was found to be a novel transient directing group enable Pd-catalyzed direct selenylation of inert C(sp2)–H bonds benzaldehydes. Diverse diarylselenides were readily constructed in high efficiency and satisfactory yields with good functional tolerance. The practical usage the method further demonstrated by enlarged reaction gram scale application facile access two selenoxanthenes one fluorescent probe.

Language: Английский

Citations

47
Diorganyl diselenides: a powerful tool for the construction of selenium containing scaffolds DOI
Amol D. Sonawane,

Rohini A. Sonawane,

Masayuki Ninomiya

et al.

Dalton Transactions, Journal Year: 2021, Volume and Issue: 50(37), P. 12764 - 12790

Published: Jan. 1, 2021

Organoselenium compounds find versatile applications in organic synthesis, materials and ligand chemistry.

Language: Английский

Citations

37
Study and Applications of Tetrasubstituted Hypervalent Selenium–Halogen Species in Catalytic Electrophilic Halogenations DOI Creative Commons
Junjie Yang,

Yung‐Yin Chan,

Weida Feng

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(4), P. 2386 - 2395

Published: Feb. 1, 2023

Electrophilic halogenation reactions are highly useful in various areas. N-Haloamides commonly used as halogen sources because of high stability and commercial availability. In order to activate N-haloamides, Lewis basic chalcogens catalysts site-isolate the strongly coordinating amide moieties. However, corresponding trisubstituted chalcogenonium–halogen cationic intermediate is sensitive moisture nucleophiles, leading poor compatibility some reactions. Herein, we report an efficient catalytic protocol using phenyl selenium with ortho-substituted carboxylic acid catalyst. Mechanistic study suggests that a tetrasubstituted neutral hypervalent Se–halogen species responsible for reactivity. This active was found be moisture-stable, system applicable wide range electrophilic functionalization including haloamidation, intermolecular haloesterification, halocycloetherification, halolactonization, aromatic halogenation, halopolyene cyclization, selenylation

Language: Английский

Citations

14
Transition metal catalysed direct selanylation of arenes and heteroarenes DOI
Daniel S. Rampon, Eduardo Q. Luz, David B. Lima

et al.

Dalton Transactions, Journal Year: 2019, Volume and Issue: 48(27), P. 9851 - 9905

Published: Jan. 1, 2019

Recent outstanding advances in the C–Se bond formation through transition metalcatalysed direct selanylation, providing new insights into their mechanistic aspects, were provided this perspective.

Language: Английский

Citations

38