Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

Chemical Reviews, Год журнала: 2022, Номер 122(21), С. 16110 - 16293

Опубликована: Сен. 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.

Язык: Английский

---

Decoding Directing Groups and Their Pivotal Role in C−H Activation

Chemistry - A European Journal, Год журнала: 2021, Номер 27(49), С. 12453 - 12508

Опубликована: Май 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.

Язык: Английский

---

Chelation-assisted transition metal-catalysed C–H chalcogenylations

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(8), С. 1022 - 1060

Опубликована: Янв. 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.

Язык: Английский

---

Electrochemical Regioselective C(sp²)–H Selenylation and Sulfenylation of Substituted 2-Amino-1,4-naphthoquinones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(2), С. 1049 - 1060

Опубликована: Янв. 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.

Язык: Английский

---

The crucial role of silver(i)-salts as additives in C–H activation reactions: overall analysis of their versatility and applicability

Chemical Society Reviews, Год журнала: 2023, Номер 52(18), С. 6359 - 6378

Опубликована: Янв. 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.

Язык: Английский

---

Electrochemical Selenylation of Sulfoxonium Ylides for the Synthesis of gem-Diselenides as Antimicrobials against Fungi

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 5572 - 5585

Опубликована: Апрель 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.

Язык: Английский

---

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

Organic Letters, Год журнала: 2019, Номер 21(17), С. 6914 - 6918

Опубликована: Авг. 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.

Язык: Английский

---

Diorganyl diselenides: a powerful tool for the construction of selenium containing scaffolds

Dalton Transactions, Год журнала: 2021, Номер 50(37), С. 12764 - 12790

Опубликована: Янв. 1, 2021

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

Язык: Английский

---

Study and Applications of Tetrasubstituted Hypervalent Selenium–Halogen Species in Catalytic Electrophilic Halogenations

ACS Catalysis, Год журнала: 2023, Номер 13(4), С. 2386 - 2395

Опубликована: Фев. 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

Язык: Английский

---

Transition metal catalysed direct selanylation of arenes and heteroarenes

Dalton Transactions, Год журнала: 2019, Номер 48(27), С. 9851 - 9905

Опубликована: Янв. 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.

Язык: Английский

---