Benzyl thioether formation merging copper catalysis DOI Creative Commons
Bing Xu, Ying‐Chih Lin, Yang Ye

et al.

RSC Advances, Journal Year: 2021, Volume and Issue: 12(2), P. 692 - 697

Published: Dec. 23, 2021

A novel copper-catalyzed thioetherification reaction has been developed to afford benzyl thioethers in moderate excellent yields. Under the mild and easy-to-operate conditions, a variety of are efficiently prepared from readily available alcohols (primary, secondary, tertiary) thiols presence Cu(OTf)2 as Lewis acid catalysis. This C-S bond formation protocol furnishes exceptional chemoselectivity, preliminary mechanism studies show that should proceed through Lewis-acid-mediated SN1-type nucleophilic attack carbocations formed situ.

Language: Английский

Chemoselective Heterogeneous Hydrogenation of Sulfur Containing Quinolines under Mild Conditions DOI Creative Commons

Lukas Lückemeier,

Thijs De Vos,

Lisa Schlichter

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(9), P. 5864 - 5871

Published: Feb. 20, 2024

Sulfur, alongside oxygen and nitrogen, holds a prominent position as one of the key heteroatoms in nature medicinal chemistry. Its significance stems from its ability to adopt different oxidation states, rendering it valuable both polarity handle hydrogen bond donor/acceptor. Nevertheless, poisonous free electron pairs makes sulfur containing substrates inaccessible for many catalytic protocols. Strong (at low temperatures) irreversible chemisorption catalyst's surface is particular detrimental heterogeneous catalysts, possessing only few catalytically active sites. Herein, we present novel Ru-S catalyst that tolerates multiple functionalities, including thioethers, thiophenes, sulfoxides, sulfones, sulfonamides, sulfoximines, hydrogenation quinolines. The utility products was further demonstrated by subsequent diversifications functionalities.

Language: Английский

Citations

19

Cobalt-catalyzed dehydrogenative functionalization of alcohols: Progress and future prospect DOI
Ishani Borthakur,

Anirban Sau,

Sabuj Kundu

et al.

Coordination Chemistry Reviews, Journal Year: 2021, Volume and Issue: 451, P. 214257 - 214257

Published: Oct. 28, 2021

Language: Английский

Citations

77

The green chemistry paradigm in modern organic synthesis DOI
Sergei G. Zlotin, Ksenia S. Egorova, Valentine P. Ananikov

et al.

Russian Chemical Reviews, Journal Year: 2023, Volume and Issue: 92(12), P. RCR5104 - RCR5104

Published: Dec. 1, 2023

After the appearance of green chemistry concept, which was introduced in vocabulary early 1990s, its main statements have been continuously developed and modified. Currently, there are 10–12 cornerstones that should form basis for an ideal chemical process. This review analyzes accumulated experience achievements towards design products processes reduce or eliminate use generation hazardous substances. The presents views leading Russian scientists specializing various fields this subject, including homogeneous heterogeneous catalysis, fine basic organic synthesis, electrochemistry, polymer chemistry, based on bio-renewable feedstocks energetic compounds materials. A new approach to quantitative evaluation environmental friendliness by authors is described. <br> bibliography includes 1761.

Language: Английский

Citations

39

Enhanced Hydride Donation Achieved Molybdenum Catalyzed Direct N-Alkylation of Anilines or Nitroarenes with Alcohols: From Computational Design to Experiment DOI
Weikang Li, Ming Huang, Jiahao Liu

et al.

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(16), P. 10377 - 10382

Published: Aug. 5, 2021

An example of homogeneous Mo-catalyzed direct N-alkylation anilines or nitroarenes with alcohols is presented. The DFT aimed design suggested the easily accessible bis-NHC-Mo(0) complex features a strong hydride-donating ability, achieving effective challenging alcohols. enhanced strategy should be useful in designing highly active systems for borrowing hydrogen transformations.

Language: Английский

Citations

50

Metal-Free, Acid/Phosphine-Induced Regioselective Thiolation of p-Quinone Methides with Sodium Aryl/Alkyl Sulfinates DOI
Biquan Xiong,

Shipan Xu,

Yu Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(2), P. 1516 - 1527

Published: Jan. 7, 2021

A simple and efficient method for the regioselective thiolation of p-quinone methides with sodium aryl/alkyl sulfinates has been established using an acid/phosphine-induced radical route under transition-metal-free conditions. broad range (p-QMs) are compatible reaction, giving expected products good to excellent yields. Control experiments were also performed gain insights into generation mechanism thiyl radicals hydrogen-atom transfer process. This protocol provides a safe feasible way formation carbon–sulfur bonds.

Language: Английский

Citations

29

Synergistic conversion of acid gases (H2S and CO2) to valuable chemicals: Carbonyl sulfide synthesis over vacancy-defective CoMo sulfide catalysts DOI
Fenglian Zhang, Zheng Wei, Guoxia Jiang

et al.

Applied Catalysis B Environment and Energy, Journal Year: 2022, Volume and Issue: 319, P. 121912 - 121912

Published: Aug. 27, 2022

Language: Английский

Citations

22

Rapid C–S Coupling in Water via Ion-Pair-Catalyzed Dehydration DOI

Yufei Zhu,

Chao Yang, Qianchi Lin

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 22, 2025

The C–S bond is of significant importance due to its unique properties and diverse roles in chemistry, biology, materials science. In this work, we present an efficient synthetic protocol a rapidly dehydrative coupling reaction with alcohols thiols water catalyzed by triaryl-carbenium ion pair. Under metal-free conditions, wide range thioethers were obtained good yields (up 99%) excellent functional group tolerance, including the fast modification amino acid derivatives molecules. This method allowed reactions be conducted low catalyst loading, down 1.0 mol %, was practical for gram-scale synthesis. Furthermore, performed under biocompatible making approach highly suitable potential bioconjugation.

Language: Английский

Citations

0

Visible-Light-Promoted Thiolation of Benzyl Chlorides with Thiosulfonates via a Photoactive Electron Donor–Acceptor Complex DOI
Chao Gong,

Jialun Huang,

Liuyan Cai

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(13), P. 9450 - 9461

Published: June 13, 2024

Visible-light-promoted thiolation of benzyl chlorides with thiosulfonates is disclosed via an electron donor-acceptor complex strategy. In addition to efficiently delivering a series arylbenzylsulfide compounds, versatile thioglycosides were also successfully constructed by applying the metal- and photocatalyst-free protocol. Preliminary mechanistic studies suggest that radical-radical coupling process was involved in this transformation.

Language: Английский

Citations

3

Biocompatible C-S bond construction for diarylmethyl thioethers DOI Creative Commons
Zhenwei Zhang, Tao Xu,

C. Ju

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: March 1, 2025

Language: Английский

Citations

0

Iron-Mediated One-Pot Dehydroxylative Cross-Electrophile Coupling of Alcohol with Disulfide for Thioether Synthesis by Using TCT as a Hydroxyl-Activating Agent DOI
Mengke Xu, X. Zhang, Yongqing Xu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 8, 2025

An efficient dehydroxythiolation between alcohols and disulfides using the widely abundant cheapest iron as a reaction mediator was developed. The one-pot thiolation proceeded effectively via C-O bond activation with aid of cyanuric chloride (TCT) hydroxyl-activating agent to give corresponding thioethers in modest excellent yields, displaying both wide substrate scope (applicable benzyl alcohol, allyl primary alkyl alcohol) good functional group tolerance. In addition, diselenide also proven be an appropriate for protocol, could subjected scale-up synthesis. Preliminary mechanistic examination revealed that transiently formed TCT-derived ether A, which is generated situ TCT possibly serves pivotal intermediate cross-electrophile thioetherification.

Language: Английский

Citations

0