Recent advances in intermolecular 1,2-difunctionalization of alkenes involving trifluoromethylthiolation

Trifluoromethylthiolative difunctionalization of alkenes, a cheap and abundant feedstock, which installs a trifluoromethylthiol (SCF3) group and another unique functional group across the carbon–carbon double bonds, provides an ideal strategy for the preparation of β-functionalized alkyl trifluoromethyl sulfides and has become a hot topic recently. This review aims to summarize the major progress in this exciting research area, with particular emphasis on the mechanistic aspects of the reaction pathways.

[1]  A. Ebadi,et al.  Transition-metal catalyzed carboxylation of organoboron compounds with CO2 , 2021 .

[2]  A. Ebadi,et al.  Oxidative trifluoromethyl(thiol/selenol)ation of terminal alkynes: An overview , 2021 .

[3]  Zunyao Wang,et al.  Oxidation of benzophenone-3 in aqueous solution by potassium permanganate: kinetics, degradation products, reaction pathways, and toxicity assessment , 2021, Environmental Science and Pollution Research.

[4]  J. Chen,et al.  Products distribution and contribution of (de)chlorination, hydroxylation and coupling reactions to 2,4-dichlorophenol removal in seven oxidation systems. , 2021, Water research.

[5]  Zunyao Wang,et al.  Effective degradation of 2,4-dihydroxybenzophenone by zero-valent iron powder (Fe0)-activated persulfate in aqueous solution: Kinetic study, product identification and theoretical calculations. , 2021, The Science of the total environment.

[6]  Yi Pan,et al.  Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes , 2021, Beilstein journal of organic chemistry.

[7]  E. Vessally,et al.  Recent trends in the direct oxyphosphorylation of C–C multiple bonds , 2020, RSC advances.

[8]  Shuai Liang,et al.  Photocatalyzed Dual-Oxidative Trifluoromethylthio-Trifluoromethylation of Alkenes with CF 3 SO 2 Na , 2020 .

[9]  Ren‐Jie Song,et al.  Recent Advances in Silver‐Mediated Radical Difunctionalization of Alkenes , 2020 .

[10]  N. Mert,et al.  Direct sulfonamidation of (hetero)aromatic C–H bonds with sulfonyl azides: a novel and efficient route to N-(hetero)aryl sulfonamides , 2020, RSC advances.

[11]  Zhenhua Ding,et al.  Recent progress of 1,1-difunctionalization of olefins. , 2020, Organic & biomolecular chemistry.

[12]  M. Lautens,et al.  Copper-Catalyzed Borylative Difunctionalization of π-Systems , 2020 .

[13]  Fatima Rashid Sheykhahmad,et al.  1,2‐(hydr)oxy-trifluoromethylation of C C multiple bonds: Synthesis of β-trifluoromethyl alcohols and α-trifluoromethyl ketones , 2020 .

[14]  Jin‐Bao Peng Recent Advances in Carbonylative Difunctionalization of Alkenes , 2020 .

[15]  Zhiping Li,et al.  Copper-catalyzed trifluoromethylthiolation-peroxidation of alkenes and allenes , 2020, Organic Chemistry Frontiers.

[16]  W. Guan,et al.  Degradation of an Organic Dye by Bisulfite Catalytically Activated with Iron Manganese Oxides: The Role of Superoxide Radicals , 2020, ACS omega.

[17]  N. Shibata,et al.  Contribution of Organofluorine Compounds to Pharmaceuticals , 2020, ACS omega.

[18]  Peifang Wang,et al.  Aryl sulfonyl chlorides and sodium aryl sulfinates: non-volatile, non-stench, and non-toxic aryl thiol surrogates for direct aryl-sulfenylation of C–H bonds , 2020, Journal of Sulfur Chemistry.

[19]  Sheng Zhu,et al.  Recent Advances in Nickel-Catalyzed Three-Component Difunctionalization of Unactivated Alkenes , 2020, Synthesis.

[20]  K. Jermsittiparsert,et al.  Methods for the direct synthesis of thioesters from aldehydes: a focus review , 2020, Journal of Sulfur Chemistry.

[21]  Xin‐Yuan Liu,et al.  Recent advances in copper-catalysed radical-involved asymmetric 1,2-difunctionalization of alkenes. , 2019, Chemical Society reviews.

[22]  O. Muzik,et al.  Fluorine-18-Labeled PET Radiotracers for Imaging Tryptophan Uptake and Metabolism: a Systematic Review , 2019, Molecular Imaging and Biology.

[23]  Somayeh Mohammadi,et al.  Convenient and robust catalyst/ligand-free synthesis of benzazole-2-ones through the reaction of aniline derivatives and sodium cyanate in aqueous medium , 2019 .

[24]  E. Vessally,et al.  Recent advances in direct trifluoromethylation of olefinic C–H bonds , 2019, RSC advances.

[25]  E. Vessally,et al.  Direct C-H trifluoromethylthiolation of (hetero)arenes: A review , 2019, Journal of Fluorine Chemistry.

[26]  P. Anbarasan,et al.  Trifluoromethylthiolative 1,2-difunctionalization of alkenes with diselenides and AgSCF3. , 2019, Chemical communications.

[27]  E. Vessally,et al.  Recent trends in direct mono-, di-, and tri-fluoromethyl(thiol)ation of S-H bonds , 2019, Journal of Sulfur Chemistry.

[28]  S. Arshadi,et al.  Recent advances in decarboxylative trifluoromethyl(thiol)ation of carboxylic acids , 2019, Journal of Fluorine Chemistry.

[29]  S. Arshadi,et al.  Direct C–H bond sulfenylation of (Het)arenes using sulfonyl hydrazides as thiol surrogate: a review , 2019, Journal of Sulfur Chemistry.

[30]  S. Ahmadi,et al.  Nano-ceria (CeO2): An efficient catalyst for the multi-component synthesis of a variety of key medicinal heterocyclic compounds , 2018 .

[31]  Guillaume Dagousset,et al.  Direct Trifluoromethylthiolation Reactions Involving Radical Processes , 2018, Synthesis.

[32]  G. C. Fu,et al.  Visible-Light-Induced, Copper-Catalyzed Three-Component Coupling of Alkyl Halides, Olefins, and Trifluoromethylthiolate to Generate Trifluoromethyl Thioethers. , 2018, ACS catalysis.

[33]  Yong Guo,et al.  Oxidative radical phosphonotrifluoromethylthiolation of unactivated alkenes with alkyl phosphonate, silver(I) trifluoromethanethiolate and potassium persulfate , 2018, Tetrahedron.

[34]  Tian Qin,et al.  Catalytic Regio- and Enantioselective Oxytrifluoromethylthiolation of Aliphatic Internal Alkenes by Neighboring Group Assistance. , 2018, Organic letters.

[35]  Ren‐Jie Song,et al.  Recent Advances in the Intermolecular Oxidative Difunctionalization of Alkenes. , 2018, Chemical record.

[36]  E. Vessally,et al.  Recent advances in sulfur–nitrogen bond formation via cross-dehydrogenative coupling reactions , 2018, RSC advances.

[37]  E. Vessally,et al.  Transition-metal-catalyzed C–N cross-coupling reactions of N-unsubstituted sulfoximines: a review , 2018 .

[38]  Liping Zheng,et al.  Oxidative Radical Intermolecular Trifluoromethylthioarylation of Styrenes by Arenediazonium Salts and Copper(I) Trifluoromethylthiolate. , 2018, The Journal of organic chemistry.

[39]  Wei Zhang,et al.  Fluoroalkylsulfonyl Chlorides Promoted Vicinal Chloro-fluoroalkylthiolation of Alkenes and Alkynes. , 2018, Organic letters.

[40]  Xiang Liu,et al.  Chiral Selenide-Catalyzed Enantioselective Allylic Reaction and Intermolecular Difunctionalization of Alkenes: Efficient Construction of C-SCF3 Stereogenic Molecules. , 2018, Journal of the American Chemical Society.

[41]  K. Didehban,et al.  S-arylation of 2-mercaptobenzazoles: a comprehensive review , 2018 .

[42]  K. Didehban,et al.  Recent advantages in the metal (bulk and nano)-catalyzed S-arylation reactions of thiols with aryl halides in water: a perfect synergy for eco-compatible preparation of aromatic thioethers , 2018 .

[43]  Yiming Jia,et al.  Fe2O3-Promoted Intermolecular Chlorotrifluoromethylthiolation of Alkenes. , 2018, The Journal of organic chemistry.

[44]  M. Beller,et al.  Photo- and Electrochemical Valorization of Carbon Dioxide Using Earth-Abundant Molecular Catalysts , 2018, Topics in Current Chemistry.

[45]  Yong‐Min Liang,et al.  Three-component difluoroalkylation and trifluoromethylthiolation/trifluoromethylselenolation of π-bonds. , 2018, Chemical communications.

[46]  Xiaodan Zhao,et al.  Combination of Lewis Basic Selenium Catalysis and Redox Selenium Chemistry: Synthesis of Trifluoromethylthiolated Tertiary Alcohols with Alkenes. , 2017, Organic letters.

[47]  F. Qing,et al.  Copper-Assisted Oxidative Trifluoromethylthiolation of 2,3-Allenoic Acids with AgSCF3. , 2017, Organic letters.

[48]  F. Liu,et al.  Photoredox-catalysed chloro-, bromo- and trifluoromethylthio-trifluoromethylation of unactivated alkenes with sodium triflinate. , 2017, Chemical communications.

[49]  M. Akita,et al.  Photocatalytic Trifluoromethylthiolation of Aromatic Alkenes Associated with Hydroxylation and Alkoxylation , 2017 .

[50]  Q. Shen,et al.  N-Trifluoromethylthio-dibenzenesulfonimide: A Shelf-Stable, Broadly Applicable Electrophilic Trifluoromethylthiolating Reagent. , 2016, The Journal of organic chemistry.

[51]  D. Cahard,et al.  State-of-the-Art in Electrophilic Trifluoromethylthiolation Reagents , 2016 .

[52]  Huidong Zheng,et al.  Recent advances in trifluoromethylthiolation using nucleophilic trifluoromethylthiolating reagents , 2016 .

[53]  Wei Zhu,et al.  Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II-III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas. , 2016, Chemical reviews.

[54]  Jun Wang,et al.  1,4-Diazabicyclo[2.2.2]octane-Promoted Aminotrifluoromethylthiolation of α,β-Unsaturated Carbonyl Compounds: N-Trifluoromethylthio-4-nitrophthalimide Acts as Both the Nitrogen and SCF3 Sources. , 2015, Organic letters.

[55]  Jin‐Hong Lin,et al.  Recent Advances in C—H Trifluoromethylthiolation and Trifluoromethoxylation Reactions , 2015 .

[56]  M. D. Hill,et al.  Applications of Fluorine in Medicinal Chemistry. , 2015, Journal of medicinal chemistry.

[57]  Yannan Liu,et al.  Diaryl Selenide Catalyzed Vicinal Trifluoromethylthioamination of Alkenes. , 2015, Organic letters.

[58]  N. Shibata,et al.  Synthetic methods for compounds having CF3-S units on carbon by trifluoromethylation, trifluoromethylthiolation, triflylation, and related reactions. , 2015, Chemical Reviews.

[59]  F. Toulgoat,et al.  Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept , 2014 .

[60]  V. Grushin The organometallic fluorine chemistry of palladium and rhodium: studies toward aromatic fluorination. , 2010, Accounts of chemical research.