Recent advances in thiolation via sulfur electrophiles

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(23), P. 6684 - 6707

Published: Jan. 1, 2022

This review systematically summarizes the recent developments for constructing sulfur compounds from electrophiles, and mechanism mainly involved thirranium ions, ylides, C–S cross coupling electrophilic substitution.

Language: Английский

---

Visible-Light-Promoted Selective Sulfonylation and Selenylation of Dienes to Access Sulfonyl-/Seleno-benzazepine Derivatives

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4208 - 4213

Published: May 30, 2023

A novel visible-light-promoted selective sulfonylation and selenylation of dienes with selenosulfonates has been developed. This technology provides mild access to a wide range sulfonyl benzo[b]azepinones seleno-benzo[b]azepines. Preliminary mechanistic studies suggest that the involves radical engaged cascade process, is accomplished through sequential oxidation/electrophilic cyclization process. The large-scale operation late-stage modification experiment reveal promising utility this protocol.

Language: Английский

---

Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation

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

---

Radical-mediated photoredox hydroarylation with thiosulfonate

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(19), P. 2767 - 2770

Published: Jan. 1, 2023

Radical-mediated photoredox hydroarylation reaction of unactivated alkenes using thiosulfonate compounds as key radical precursors to synthesize pyridyquinazolinone and pyrroloquinazolinone derivatives is described.

Language: Английский

---

Visible-light induced direct C(sp³)–H functionalization: recent advances and future prospects

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5278 - 5305

Published: Jan. 1, 2024

This review summarizes the latest methodological advances in photocatalytic C(sp 3 )–H functionalization, with a particular emphasis on formation of C–P, C–B, C–S bonds, etc ., and some prominent efforts asymmetric C–H functionalization.

Language: Английский

---

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

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

---

Photocatalytic Sulfonylation: Innovations and Applications

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 14, 2024

Photosynthesis, converting sustainable solar energy into chemical energy, has emerged as a promising craft to achieve diverse organic transformations due its mild reaction conditions, sustainability, and high efficiency. The synthesis of sulfonated compounds drawn significant attention in the pharmaceuticals, agrochemicals, materials industries unique structure electronic properties sulfonyl groups. Over past decades, many photocatalytic sulfonylation reactions have been developed. In this review, recent advances photocatalyzed reviewed since 2020, with primary focus on discussing design mechanism.

Language: Английский

---

Sulfoxidation of pyrimidine thioate derivatives and study their biological activities

Scientific Reports, Journal Year: 2025, Volume and Issue: 15(1)

Published: Jan. 6, 2025

Abstract In a quest to innovate biologically active molecules, the benzoylation of 4,6-dimethylpyrimidine-2-thiol hydrochloride ( 1 ) with benzoyl chloride derivatives was employed produce series pyrimidine benzothioate 2–5 ). Subsequent sulfoxidation these using hydrogen peroxide and glacial acetic acid yielded diverse array sulfonyl methanone 6–9 parallel, sulfonothioates 10–12 pyrimidines 13–15 ), originating from condensation compound derivatives. The newly synthesized compounds underwent characterization via FT-IR, NMR, mass spectrometry, elemental analyses. Biological screenings unveiled interesting properties: 6 exhibited significant antimicrobial potency against S. epidermidis haemolyticus , whereas 11 showed distinct insensitivity. Excitingly, 12 showcased robust antioxidant activity by efficiently scavenging DPPH • radical, underscoring their potential in oxidative stress mitigation. Notably, 10 displayed promising anti-tumor effects, demonstrating superior efficacy MCF-7 breast cancer cell line compared . study revealed spectrum biological activities across derivatives, modifications often resulting diminished bioactivity parent These findings shed light on intricate relationship between chemical properties, offering valuable insights for future drug discovery endeavors.

Language: Английский

---

Visible-Light-Induced Energy-Transfer-Mediated Hydrofunctionalization and Difunctionalization of Unsaturated Compounds via Sigma-Bond Homolysis of Energy-Transfer Acceptors

ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(3), P. 1854 - 1941

Published: Jan. 17, 2025

Over the past decade, visible-light-mediated energy-transfer (EnT) catalysis, particularly triplet–triplet (TTEnT) has emerged as a mild and environmentally friendly approach for diverse organic synthetic transformations. In contrast to photoredox which typically requires sacrificial electron donors or acceptors complete catalytic cycle, EnT photocatalysis generally proceeds with high atom economy while minimizing generation of wasteful byproducts. Furthermore, successful catalysis is contingent upon precise control redox potentials both photocatalysts substrates, strategies are primarily influenced by triplet energy compatibility between these entities. Considering growing importance photocatalysis, well hydrofunctionalization difunctionalization reactions in synthesis, this review systematically summarizes significant advancements EnT-enabled unsaturated compounds via sigma-bond homolysis over decade. Special emphasis placed on elucidating substrate scopes mechanistic scenarios. Additionally, discusses versatile applications methodologies addresses current challenges opportunities within evolving research field. This structured into six main categories based different types sigma-bonds undergoing homolysis. These include transformations mediated 1) N–O bond oxime esters other N,O-radical precursors; 2) N–S N-sulfonyl imines N,S-radical 3) chalcogen–chalcogen disulfides oxy/thio/selenosulfonates; 4) C–S tri/difluoromethylated sulfinates, acetylenic triflones, arylsulfonium salts; 5) C–X (X = halogen) halides; 6) acceptors. Through providing theoretical backgrounds along comprehensive overview currently employed acceptors, photosensitizers, contemporary EnT-induced compounds, aims serve an invaluable resource future innovations rapidly

Language: Английский

---

Selenium Electrophilic Center Responsive to Biological Electron Donors for Efficient Chemotherapy

Advanced Science, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 14, 2025

Abstract Designing drugs to intelligently respond different ratio of biological electron donors/receptors in cancer cells and normal is a promising strategy achieve highly effective less toxic chemotherapy. Herein by employing metal center active the selenium‐containing electrophilic drug Ru(phtpy‐NO 2 )(phenSe)Cl ( RuSe ) with strongly polarization characteristics are synthesized which can efficiently shuttle electrons from donors convert oxidative stress. The rate transfer at selenium 1.81 times higher cell environments compared environments. This results being 14.98 more lethal than cells. Experimental demonstrate that transport process carried out via radicals intermediate positively correlated properties atoms. transports bioactive generate large number superoxide anions leading DNA damage decrease mitochondrial membrane potential further activates p53 signaling pathway amplifies cell‐killing effect after transporting electrons. work provides new avenue for design efficient chemotherapeutic agents.

Language: Английский

---