4.5 Review

Recent Metal-Catalyzed Methods for Thioether Synthesis

Related references

Note: Only part of the references are listed.
Article Chemistry, Applied

Gold-Catalyzed Reactions of 2-Alkynyl-1-indolyl-1,2-diols with Thiols: Stereoselective Synthesis of (Z)-α-Indol-3-yl α-(2-Thioalkenyl) Ketones

Fernando Martinez-Lara et al.

Summary: The gold-catalyzed transformation of propargylic glycols with thiols results in the formation of alpha-indol-3-yl alpha-((Z)-2-thioalkenyl) ketones through a complex but selective reaction mechanism. This sequence involves regioselective thiolation of indolyl diols followed by the attack of sulfur on the activated alkyne, rather than the indole. The final compounds are obtained in high yields from simple starting materials such as indolyl acyloins, ethynyl magnesium bromide, and thiols.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Article Chemistry, Physical

Acetate Facilitated Nickel Catalyzed Coupling of Aryl Chlorides and Alkyl Thiols

Regina M. Oechsner et al.

Summary: We present a catalytic system that allows for mild and fast coupling of aryl chlorides with primary, secondary, and previously challenging tertiary alkyl thiols using an air-stable nickel(II) precatayst in combination with cost-effective potassium acetate as a base at room temperature. This system exhibits excellent tolerance towards various functional groups and yields thioethers in high yields, including pharmaceutical compounds. The chemoselective functionalization of disubstituted substrates is successfully demonstrated.

ACS CATALYSIS (2022)

Review Chemistry, Organic

Nickel-Catalyzed Paired Electrochemical Cross-Coupling of Aryl Halides with Nucleophiles

Yong Zhang et al.

Summary: Electrochemistry has gained attention as a versatile strategy in synthetic organic chemistry. Paired electrochemical reactions can improve atom economy and energy efficiency.

SYNTHESIS-STUTTGART (2022)

Review Chemistry, Organic

Recent Trends in Nickel-Catalyzed C-S Bond Formation

U. S. Kanchana et al.

Summary: This review summarizes the latest advancements in nickel-catalyzed C-S bond formation reactions, which have attracted attention due to their wide application and the substitution of toxic metals.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Thiolate-assisted copper(i) catalyzed C-S cross coupling of thiols with aryl iodides: scope, kinetics and mechanism

Sneha Prasad Bakare et al.

Summary: A Cu(i) catalyst is used in an efficient method for the C-S cross coupling of thiophenols with aryl iodides, resulting in good to excellent yields of diaryl sulfides. The reactions proceed smoothly in polar protic solvents and under ligand-free environments. This method also finds application in the synthesis of 2-aminophenyl sulfide derivatives.

NEW JOURNAL OF CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Safe, Scalable, Inexpensive, and Mild Nickel-Catalyzed Migita-Like C-S Cross-Couplings in Recyclable Water

Tzu-Yu Yu et al.

Summary: A new method of C-S coupling based on nickel catalysis in water with micellar catalysis has been reported, showing high isolated yields under mild conditions. It offers potential for scalability and low residual metal content, making it applicable to pharmaceutical synthesis targets. The associated low E Factor also suggests it may be a more attractive option compared to current methods using unsustainable Pd catalyst loadings.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Electroreductive Nickel-Catalyzed Thiolation: Efficient Cross-Electrophile Coupling for C-S Formation

Nate W. J. Ang et al.

Summary: In this research, an efficient and mild electrochemical thiolation method was developed for the synthesis of alkyl sulfides by cross-electrophile coupling of alkyl bromides with bench-stable thiosulfonates. Mechanistic insights into this electrocatalytic thiolation reaction were elucidated through cyclic voltammetry and potentiostatic analysis.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Organic

Copper-Catalyzed Selective Defluorinative Sulfuration of Trifluoropropanamides Leading to α-Fluorothioacrylamides

Xiao-Qin Shen et al.

Summary: A practical and efficient method for synthesizing alpha-fluorothioacrylamide was developed through selective defluorinative sulfuration of trifluoropropanamides with disulfides. The N-chelation-assisted copper-catalyzed defluorination and sulfurization reactions show excellent functional group tolerance and incorporation of both sulfur atoms of disulfides into acrylamides.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Inorganic & Nuclear

Mono- and Dinuclear α-Diimine Nickel(II) and Palladium(II) Complexes in C-S Cross-Coupling

Md Muktadir Talukder et al.

Summary: In this study, highly air- and moisture-stable transition metal catalytic systems for C-S cross-coupling reactions were reported. These systems exhibited broader substrate scope and functional group tolerance than previously reported catalysts, with over 40 compounds synthesized from thiols. The five-coordinate bridged dinuclear Ni complex outperformed other complexes by giving almost quantitative yields across a broad substrate scope.

ORGANOMETALLICS (2021)

Article Chemistry, Organic

Paired Electrolysis Enabled Ni-Catalyzed Unconventional Cascade Reductive Thiolation Using Sulfinates

Jun-Chen Kang et al.

Summary: This study reports a nickel-catalyzed cascade reductive thiolation of aryl halides with sulfinates driven by paired electrolysis, enabling the synthesis of various thioethers under mild conditions. Mechanistic exploration reveals that a cascade chemical step can occur at the electrode interface and potentially alter the reaction pathway in paired electrolysis, leading to the discovery of novel cascade reactions with unique reactivity.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Preparation of Recyclable and Versatile Porous Poly(aryl thioether)s by Reversible Pd-Catalyzed C-S/C-S Metathesis

Miguel A. Rivero-Crespo et al.

Summary: This study introduces a new family of porous poly(aryl thioether)s synthesized via a Pd-catalyzed C-S/C-S metathesis-based method, combining the attractive properties of porous polymers and poly(phenylene sulfide). These materials show excellent chemical resistance and recyclability, making them suitable for various environmentally relevant applications.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters

Fusheng Bie et al.

Summary: The Pd-catalyzed double-decarbonylative synthesis of aryl thioethers involves an aryl exchange reaction between amides and thioesters, with amides serving as aryl donors and thioesters as sulfide donors. The use of Pd/Xantphos without any additives promotes aryl exchange by C(O)-N/C(O)-S cleavages, allowing for a wide variety of amides and sulfides to be used in the reaction.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Rhodium-Catalyzed Twofold Unsymmetrical C-H Alkenylation-Annulation/Thiolation Reaction To Access Thiobenzofurans

Jian Lin et al.

Summary: A Rh(III)-catalyzed twofold unsymmetrical C-H alkenylation-annulation/thiolation reaction has been developed for the efficient synthesis of varied thiobenzofurans in a straightforward manner. This protocol demonstrates good functional group tolerance and broad substrate scope under mild reaction conditions.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

An Efficient, Sustainable Rhodium-Catalyzed and Ionic Liquid-Mediated C-H Thiolation and Selenation of Acetanilide with Diaryl Disulfides and Diaryl Diselenides

Xiyan Rui et al.

Summary: The method utilizes rhodium(III) catalysis and ionic liquid to achieve efficient and sustainable C-S and C-Se formation from acetanilide with diaryl disulfides or diaryl diselenides, demonstrating wide functional group compatibility and easy removal of directing group. It can serve as a straightforward approach to phenothiazine scaffold with potent biological activities, making it broadly applicable in organic synthesis and medicinal chemistry.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Applied

Palladium-Catalyzed Alkene Thioacylation: A C-S Bond Activation Approach for Accessing Indanone Derivatives

Jianing Wu et al.

Summary: A palladium-catalyzed intramolecular alkene thioacylation reaction is reported, initiated by the activation of thioester C(acyl)-S bonds, which suppresses decarbonylation and beta-hydrogen elimination with related intermediates, providing an efficient method to access indanone scaffolds. Mechanistic studies support olefin insertion into C(acyl)-Pd bonds, and further conversion of the newly formed methylene sulfide substituent demonstrates the synthetic utility of this protocol.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Redefining the Mechanistic Scenario of Carbon-Sulfur Nucleophilic Coupling via High-Valent Cp*CoIV Species

Sara Lopez-Resano et al.

Summary: The potential access to Co-IV species to promote transformations challenging at Co-III in Cp*Co-catalyzed C-H functionalization reactions remains underexploited. We reveal the participation of Cp*Co-IV species in a Cp*Co-mediated C-S bond-reductive elimination through a combined experimental and computational strategy. These studies support the intermediacy of high-valent Cp*Co species in C-H functionalization reactions, particularly when involving nucleophilic coupling partners under oxidative conditions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Synthesis of Spirocycles via Ni-Catalyzed Intramolecular Coupling of Thioesters and Olefins

Wenfei Liu et al.

Summary: A nickel-catalyzed intramolecular coupling of thioesters and olefins has been developed for the efficient synthesis of spirocycles, providing a powerful building block for the assembly of complex scaffolds commonly found in natural products.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Organic

Forging C-S(Se) Bonds by Nickel-catalyzed Decarbonylation of Carboxylic Acid and Cleavage of Aryl Dichalcogenides

Jing-Ya Zhou et al.

Summary: A nickel-catalyzed decarbonylation of carboxylic acids cross-coupling protocol has been developed for the direct formation of C-S(Se) bond, with good to excellent yields and wide substrate tolerance. The reaction can also be conducted on gram scale with good yield.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Enantioselective Hydrothiolation: Diverging Cyclopropenes through Ligand Control

Shaozhen Nie et al.

Summary: In this study, Rh-catalyzed hydrothiolation of cyclopropenes is advanced through divergent reactivity, leading to the formation of cyclopropyl sulfides or allylic sulfides. The choice of bisphosphine ligand determines whether the pathway involves ring-retention or ring-opening, with mechanistic studies revealing the origin of this switchable selectivity. Results indicate a common cyclopropyl-Rh(III) intermediate shared by the two pathways.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C-S/C-N Couplings

M. Trinidad Martin et al.

Summary: This study describes a new Ni-catalyzed C-S cross-coupling reaction that efficiently couples a wide range of (hetero)aryl halides, including challenging aryl chlorides, with various aromatic and aliphatic thiols. Additionally, it was found that aryl and alkenyl tosylates can also serve as competent electrophilic partners in the reaction.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Organic

Cp*Rh(III)-Catalyzed Regioselective C(sp3)-H Electrophilic Trifluoromethylthiolation of 8-Methylquinolines

Sumit et al.

Summary: In this study, a highly regioselective trifluoromethylthiolation of the unactivated C(sp(3))-H bond of 8-methylquinolines catalyzed by Rh(III) was explored, with good yields and high regioselectivity. The reaction conditions are also applicable for late-stage functionalization of natural molecules santonin and caffeine-substituted 8-methylquinoline.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

Ryota Isshiki et al.

Summary: A Ni-catalyzed aryl sulfide synthesis method was developed using 2-pyridyl sulfide as the sulfide donor, eliminating the need for odorous and toxic thiols. The Ni/dcypt catalyst played a crucial role in the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, with mechanistic studies showing its ability to undergo oxidative additions and ligand exchanges simultaneously.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Electrochemical Deoxygenative Thiolation of Preactivated Alcohols and Ketones

Feng Zhang et al.

Summary: This work describes a nickel-catalyzed deoxygenative thiolation of alcohols and ketones under mild conditions with electrochemical promotion. Graphene/nickel foam electrodes in an undivided cell exhibit excellent substrate tolerance and good chemical yields. Further investigation has been conducted to gain mechanistic insight into this electrochemical cross-coupling.

ORGANIC LETTERS (2021)

Article Chemistry, Physical

Mechanism of Counterion-Controlled Regioselective Hydrothiolation of 1,3-Dienes: Insights from a Density Functional Theory Study

Xiuling Wen et al.

Summary: A recent study using density functional theory investigated the mechanism of Rh-catalyzed hydrothiolation of unsymmetrical 1,3-dienes with different counterions. The results showed that counterion-controlled electronic and steric effects play a crucial role in determining the regioselectivity of the reaction, providing insights for designing more efficient catalytic systems with transition-metal complexes.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Synthesis of dithienofurans via cascade copper catalysed dual C-S coupling and ring closure reactions under mild conditions

Lu Zhou et al.

Summary: A mild catalytic approach has been developed for the synthesis of new dithienofuran derivatives via cascade copper catalysed dual C-S coupling and subsequent ring closure reactions. The strategy shows broad substrate scope and can be used to prepare aryl, heteroaryl, and alkyl substituted dithienofuran derivatives in up to 70% yields. The proposed mechanism includes a Cu(i)/Cu(iii) catalytic cycle and a subsequent Cu(ii) induced cyclization mechanism.

RSC ADVANCES (2021)

Article Chemistry, Multidisciplinary

Cp*Co(iii)-catalyzed C2-thiolation and C2,C3-dithiolation of substituted indoles with N-(arylthio)succinimide

Jayanta Ghorai et al.

Summary: A new method for thiolation of indole derivatives has been developed using N-(aryl/alkylthio)succinimide as a thiolating reagent and Cp*Co-III catalyst, which can efficiently yield thiolated products without the need for external oxidants. The importance of the Cp*Co-III catalyst for both C2- and C3-thiolation has been revealed through control experiments.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Ni-catalyzed non-activated C-S bond cleavage at ambient temperature for the synthesis of sulfur-containing polycyclic compounds

Takanori Shibata et al.

Summary: A Ni-catalyzed intramolecular reaction of diarylthioether-tethered 1,8-diynes was successfully carried out at ambient temperature, yielding sulfur-containing tetracyclic compounds. The reaction involved non-activated sp(2) C-S bond cleavage and consecutive alkyne insertions. Furthermore, the obtained cycloadduct exhibited photo-catalytic activity in benzylic oxidation.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Organic

Decarbonylative sulfide synthesis from carboxylic acids and thioesters via cross-over C-S activation and acyl capture

Chengwei Liu et al.

Summary: A method for the synthesis of sulfides from carboxylic acids via thioester C-S activation and acyl capture has been developed, allowing efficient decarbonylative thioetherification of a variety of carboxylic acids and thioesters. This method operates under mild, external base-free, and operationally practical conditions, providing a powerful new framework to unlock aryl electrophiles from carboxylic acids.

ORGANIC CHEMISTRY FRONTIERS (2021)

Review Chemistry, Organic

Metal-catalyzed C-S bond formation using sulfur surrogates

Nallappan Sundaravelu et al.

Summary: Sulfur-containing compounds have wide applications in material chemistry, with transition metal-catalyzed C-S bond-forming reactions overcoming traditional synthesis obstacles. An appropriate sulfur source and surrogate are crucial in these reactions, driving interest in the synthesis of organosulfur compounds through metal-catalyzed reactions.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides

Weigang Zhang et al.

Summary: Redox-active benzimidazolium sulfonamides have been developed as thiolating reagents for reductive C-S bond coupling. The IMDN-SO2R reagent provides a stable cationic precursor to generate highly active N-S intermediates, enabling successful cross-electrophilic coupling with various organic halides. The use of an electrophilic sulfur source has practical benefits such as broad substrate scope and excellent tolerance, while avoiding catalyst deactivation and unpleasant odors from thiols.

CHEMICAL SCIENCE (2021)

Article Chemistry, Physical

Catalytic conversion of alkynes to α-vinyl sulfides mediated by carbene-linker-carbene (CXC) rhodium and iridium complexes

Lewis C. Tolley et al.

Summary: The catalytic activity of Rh(i) and Ir(i) complexes bearing carbene-linker-carbene (CXC) bis-triazolylidene ligands in the hydrothiolation of alkynes was evaluated. Rhodium complexes showed high selectivity towards Markovnikov product formation and superior activity compared to iridium derivatives. The neutral dinuclear [Rh2Cl2(cod)(2)(mu-COC)] was found to be the most effective catalyst for this transformation, demonstrating high activity and selectivity towards the alpha-vinyl sulfide product.

CATALYSIS SCIENCE & TECHNOLOGY (2021)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Inter- and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

Tristan Delcaillau et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Applied

DABCO-promoted Diaryl Thioether Formation by Metal-catalyzed Coupling of Sodium Sulfinates and Aryl Iodides

Yanpeng Liu et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Article Chemistry, Organic

Rhodium-Catalyzed Direct ortho C-H Thiolation of Cyclic N-Sulfonyl Ketimines

Guangrui Shi et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Organic

Unconventional Reactivity with DABCO-Bis(sulfur dioxide): C-H Bond Sulfenylation of Imidazopyridines

Julie Le Bescont et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Organic

Bronsted Acid-Assisted Zinc-Catalyzed Markovnikov-Type Hydrothiolation of Alkenes Using Thiols

Nobukazu Taniguchi

JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Inorganic & Nuclear

Cobalt-Catalyzed Ligand-Controlled Divergent Regioselective Reactions of 1,6-Enynes with Thiols

Gaowei Wang et al.

ORGANOMETALLICS (2020)

Review Chemistry, Organic

Iron-Catalyzed Cross-Coupling Reactions for the Construction of Carbon-Heteroatom Bonds

Juan Zhang et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Physical

Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers

Conor E. Brigham et al.

ACS CATALYSIS (2020)

Article Chemistry, Organic

A Robust Pd-Catalyzed C-S Cross-Coupling Process Enabled by Ball-Milling

Andrew C. Jones et al.

ORGANIC LETTERS (2020)

Article Chemistry, Multidisciplinary

Gold-Catalyzed Asymmetric Thioallylation of Propiolates via Charge-Induced Thio-Claisen Rearrangement

Hanbyul Kim et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Electrochemical nickel-catalyzed Migita cross-coupling of 1-thiosugars with aryl, alkenyl and alkynyl bromides

Mingxiang Zhu et al.

CHEMICAL COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Thiolation of Aryl Halides and Heteroaryl Halides through Electrochemistry

Dong Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Organic

Achieving Nickel Catalyzed C-S Cross-Coupling under Mild Conditions Using Metal Ligand Cooperativity

Rina Sikari et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Organic

Copper-Catalyzed Double Thiolation To Access Sulfur-Bridged Imidazopyridines with Isothiocyanate

Lu-Lu Tian et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Catalytic Hydrothiolation: Counterion-Controlled Regioselectivity

Xiao-Hui Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Organic

Palladium-Catalyzed Tandem Isomerization/Hydrothiolation of Allylarenes

Prasad M. Kathe et al.

ORGANIC LETTERS (2019)

Article Chemistry, Physical

Electrochemically Promoted Nickel-Catalyzed Carbon-Sulfur Bond Formation

Yang Wang et al.

ACS CATALYSIS (2019)

Article Chemistry, Applied

Thioesters as Bifunctional Reagents for 2-Naphthylamine Sulfuracylation

Fuhong Xiao et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

Article Multidisciplinary Sciences

Nickel-catalysed selective migratory hydrothiolation of alkenes and alkynes with thiols

Yulong Zhang et al.

NATURE COMMUNICATIONS (2019)

Article Chemistry, Organic

Pd/PTABS: Low-Temperature Thioetherification of Chloro(hetero)arenes

Siva Sankar Murthy Bandaru et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Organic

Tandem Double-Cross-Coupling/Hydrothiolation Reaction of 2-Sulfenyl Benzimidazoles with Boronic Acids

Alexandra Basilio Lopes et al.

ORGANIC LETTERS (2019)

Article Chemistry, Physical

Pd-Catalyzed Alkenyl Thioether Synthesis from Thioesters and N-Tosylhydrazones

Kota Ishitobi et al.

ACS CATALYSIS (2019)

Article Chemistry, Organic

Cross-Coupling of Chloro(hetero)arenes with Thiolates Employing a Ni(0)-Precatalyst

Paul H. Gehrtz et al.

ORGANIC LETTERS (2019)

Article Chemistry, Organic

Ru(ii)-Catalysed synthesis of (1H)-isothiochromenes by oxidative coupling of benzylthioethers with internal alkynes

Esteban P. Urriolabeitia et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Controlled Ni-catalyzed mono- and double-decarbonylations of α-ketothioesters

Zhao-Jing Zheng et al.

CHEMICAL COMMUNICATIONS (2019)

Article Chemistry, Organic

Direct C-S bond formation via C-O bond activation of phenols in a crossover Pd/Cu dual-metal catalysis system

Vahid Khakyzadeh et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Facile synthesis of 1,2-thiobenzonitriles via Cu-catalyzed denitrogenative radical coupling reaction

Yao Zhou et al.

CHEMICAL COMMUNICATIONS (2019)

Article Chemistry, Organic

Nickel Phosphite/Phosphine-Catalyzed C-S Cross-Coupling of Aryl Chlorides and Thiols

Kieran D. Jones et al.

ORGANIC LETTERS (2018)

Article Chemistry, Multidisciplinary

Site-Selective C-S Bond Formation at C-Br over C-OTf and C-Cl Enabled by an Air-Stable, Easily Recoverable, and Recyclable Palladium(I) Catalyst

Thomas Scattolin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant

Jin Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Review Chemistry, Organic

Photocatalytic formation of carbon-sulfur bonds

Alexander Wimmer et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts

Chengwei Liu et al.

CHEMICAL COMMUNICATIONS (2018)

Article Chemistry, Multidisciplinary

Decarbonylative Aryl Thioether Synthesis by Ni Catalysis

Kota Ishitobi et al.

CHEMISTRY LETTERS (2018)

Review Chemistry, Multidisciplinary

Metal-Catalyzed Synthesis and Use of Thioesters: Recent Developments

Vera Hirschbeck et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

Article Chemistry, Organic

Palladium-Catalyzed Cyanothiolation of Internal Alkynes Using Organic Disulfides and tert-Butyl Isocyanide

Shinya Higashimae et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Organic

Copper-catalyzed peri-selective direct sulfenylation of 1-naphthylamines with disulfides

Yan-Shi Xiong et al.

ORGANIC CHEMISTRY FRONTIERS (2018)

Review Chemistry, Multidisciplinary

Analysis of US FDA-Approved Drugs Containing Sulfur Atoms

Kevin A. Scott et al.

TOPICS IN CURRENT CHEMISTRY (2018)

Article Chemistry, Applied

Palladium-Catalyzed Regioselective Three-Component Cascade Bisthiolation of Terminal Alkynes

Jianxiao Li et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

Article Chemistry, Multidisciplinary

Ex Situ Formation of Methanethiol: Application in the Gold(I)-Promoted Anti-Markovnikov Hydrothiolation of Olefins

Steffan K. Kristensen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Catalytic Hydrothiolation: Regio- and Enantioselective Coupling of Thiols and Dienes

Xiao-Hui Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

A Hemilabile and Cooperative N-Donor-Functionalized 1,2,3-Triazol-5-Ylidene Ligand for Alkyne Hydrothiolation Reactions

Ian Strydom et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Article Chemistry, Organic

Palladium-Catalyzed Migratory Insertion of Isocyanides into C(thiophene)-SMe Bonds: Access to Atom-Transfer Reactions

Amir Hossein Vahabi et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Organic

Nickel-Catalyzed C-S Coupling: Synthesis of Diaryl Sulfides Starting from Phenyldithiocarbamates and Iodobenzenes

Xing Liu et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Organic

Rh(III)-Catalyzed Direct ortho-Chalcogenation of Phenols and Anilines

Shiping Yang et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Inorganic & Nuclear

Scope and Mechanism of Iridium Porphyrin-Catalyzed S-H Insertion Reactions between Thiols and Diazo Esters

Taiwo O. Dairo et al.

ORGANOMETALLICS (2017)

Article Chemistry, Organic

Para-Selective C-H Thioetherification

Wei-Chieh Hsu et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Regiocontrolled direct C4 and C2-methyl thiolation of indoles under rhodium-catalyzed mild conditions

Saurabh Maity et al.

CHEMICAL COMMUNICATIONS (2017)

Article Chemistry, Multidisciplinary

Rhodium-catalyzed odorless synthesis of diaryl sulfides from borylarenes and S-aryl thiosulfonates

Kazuya Kanemoto et al.

CHEMICAL COMMUNICATIONS (2017)

Article Chemistry, Multidisciplinary

Sulfur-directed carbon-sulfur bond cleavage for Rh-catalyzed regioselective alkynylthiolation of alkynes

Takanori Shibata et al.

CHEMICAL COMMUNICATIONS (2017)

Article Chemistry, Multidisciplinary

CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl Bromides and Chloridess

Chia-Wei Chen et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Review Chemistry, Inorganic & Nuclear

Sustainable metal catalysis in C-H activation

Nikolaos V. Tzouras et al.

COORDINATION CHEMISTRY REVIEWS (2017)

Article Chemistry, Multidisciplinary

Iron(II)-catalyzed sulfur directed C(sp3)-H bond amination/C-S cross coupling reaction

Fang-Fang Duan et al.

CHEMICAL COMMUNICATIONS (2017)

Review Chemistry, Physical

Cobalt-Catalyzed C-H Activation

Marc Moselage et al.

ACS CATALYSIS (2016)

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed C-H Thiolation through Dehydrogenative Cross-Coupling

Tobias Gensch et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Aerobic copper-catalyzed decarboxylative thiolation

Minghao Li et al.

CHEMICAL COMMUNICATIONS (2016)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed C-H Chalcogenation of Anilines

Thomas Mueller et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Article Chemistry, Organic

Nickel-Catalyzed ortho-C-H Thiolation of N-Benzoyl α-Amino Acid Derivatives

Feng Gao et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Organic

Copper-Catalyzed 2,2,2-Trifluoroethylthiolation of Aryl Halides

Shouxiong Chen et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Regiodivergent Hydrothiolation of Allyl Amines and Imines

Jennifer L. Kennemur et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Organic

Gold-Catalyzed Anti-Markovnikov Selective Hydrothiolation of Unactivated Alkenes

Taichi Tamai et al.

ORGANIC LETTERS (2016)

Article Chemistry, Organic

Palladium-Catalyzed Stereoselective Formation of Substituted Allylic Thioethers and Sulfones

Jose Enrique Gomez et al.

ORGANIC LETTERS (2016)

Article Chemistry, Applied

Thiol-free route to diaryl sulfides by Cu catalyzed coupling of sodium thiosulfate with aryl halides

Najmeh Nowrouzi et al.

CHINESE JOURNAL OF CATALYSIS (2016)

Article Chemistry, Multidisciplinary

Z-Selective Hydrothiolation of Racemic 1,3-Disubstituted Allenes: An Atom-Economic Rhodium-Catalyzed Dynamic Kinetic Resolution

Adrian B. Pritzius et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Asymmetric Rhodium-Catalyzed Addition of Thiols to Allenes: Synthesis of Branched Allylic Thioethers and Sulfones

Adrian B. Pritzius et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

A Reaction of Triazoles with Thioesters to Produce β-Sulfanyl Enamides by Insertion of an Enamine Moiety into the Sulfur-Carbonyl Bond

Tomoya Miura et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

CO2-promoted oxidative cross-coupling reaction for C-S bond formation via masked strategy in an odourless way

Zongjun Qiao et al.

CHEMICAL COMMUNICATIONS (2015)

Article Chemistry, Multidisciplinary

Nickel-catalyzed thiolation of unactivated aryl C-H bonds: efficient access to diverse aryl sulfides

Sheng-Yi Yan et al.

CHEMICAL COMMUNICATIONS (2015)

Article Chemistry, Medicinal

A Survey of the Role of Noncovalent Sulfur Interactions in Drug Design

Brett R. Beno et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

Article Chemistry, Organic

NiSO4-catalyzed C-H activation/C-S cross-coupling of 1,2,3-triazole N-oxides with thiols

Jiayi Zhu et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2015)

Article Chemistry, Organic

Activation of Aryl Thiocyanates Followed by Aryne Insertion: Access to 1,2-Thiobenzonitriles

Martin Pawliczek et al.

ORGANIC LETTERS (2015)

Article Chemistry, Multidisciplinary

A novel and efficient zinc-catalyzed thioetherification of aryl halides

Amrutha P. Thankachan et al.

RSC ADVANCES (2015)

Article Chemistry, Organic

The Palladium-Catalyzed Intermolecular C-H Chalcogenation of Arenes

Renhua Qiu et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Directed Sulfenylation of Arene C-H Bonds

Yaxi Yang et al.

CHEMISTRY-A EUROPEAN JOURNAL (2014)

Article Chemistry, Multidisciplinary

[(IPent) PdCl2(morpholine)]: A Readily Activated Precatalyst for Room-Temperature, Additive-Free Carbon-Sulfur Coupling

Jennifer L. Farmer et al.

CHEMISTRY-A EUROPEAN JOURNAL (2014)

Article Chemistry, Medicinal

Data-Mining for Sulfur and Fluorine: An Evaluation of Pharmaceuticals To Reveal Opportunities for Drug Design and Discovery

Elizabeth A. Ilardi et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

Article Chemistry, Organic

Regioselective Hydrothiolation of Alkenes Bearing Heteroatoms with Thiols Catalyzed by Palladium Diacetate

Taichi Tamai et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

Article Chemistry, Multidisciplinary

Manganese-Catalyzed Cross-Coupling of Thiols with Aryl Iodides

Tsung-Jui Liu et al.

CHEMISTRY-AN ASIAN JOURNAL (2013)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Synthesis of Aryl Trifluoromethyl Sulfides at Room Temperature

Cheng-Pan Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Organic

Thiol-yne coupling: revisiting old concepts as a breakthrough for up-to-date applications

Alessandro Massi et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2012)

Letter Chemistry, Multidisciplinary

On the Role of Metal Contaminants in Catalyses with FeCl3

Stephen L. Buchwald et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Article Chemistry, Multidisciplinary

Synthesis of Aryl Sulfides by Decarboxylative C-S Cross-Couplings

Zhongyu Duan et al.

CHEMISTRY-A EUROPEAN JOURNAL (2009)

Article Hematology

Cangrelor Attenuates Coated-Platelet Formation

Nicholas B. Norgard et al.

CLINICAL AND APPLIED THROMBOSIS-HEMOSTASIS (2009)

Article Chemistry, Organic

Indium-Catalyzed C-S Cross-Coupling of Aryl Halides with Thiols

V. Prakash Reddy et al.

JOURNAL OF ORGANIC CHEMISTRY (2009)

Article Chemistry, Multidisciplinary

Iron-catalyzed S-arylation of thiols with aryl iodides

Arkaitz Correa et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

Article Chemistry, Medicinal

Conformation-activity relationship on novel 4-pyridylmethylthio derivatives with antiangiogenic activity

Takahiro Honda et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2008)

Article Chemistry, Multidisciplinary

Rhodium-catalyzed substitution reaction of aryl fluorides with disulfides:: p-orientation in the polyarylthiolation of polyfluorobenzenes

Mieko Arisawa et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Article Chemistry, Organic

Cobalt-catalyzed aryl-sulfur bond formation

Ying-Chieh Wong et al.

ORGANIC LETTERS (2006)

Article Chemistry, Multidisciplinary

A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols

MA Fernández-Rodríguez et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Organic

A general palladium-catalyzed coupling of aryl bromides/triflates and thiols

T Itoh et al.

ORGANIC LETTERS (2004)