TBAI-catalyzed selective synthesis of sulfonamides and β-aryl sulfonyl enamines: coupling of arenesulfonyl chlorides and sodium sulfinates with tert-amines.

A simple, practical and metal-free method has been developed for the synthesis of sulfonamides and β-arylsulfonyl enamines via the selective cleavage of C-N and C-H bonds through the iodine-catalyzed oxidation of arenesulfonyl chlorides and sodium sulfinates with tert-amines. The method uses commercially available inexpensive catalysts and oxidants, and has a wide substrate scope and operational simplicity.

• Publication year

  2019

• Venue

  Organic and biomolecular chemistry

• Publication date

  2019-03-06

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1039/c8ob02992jPMID 30775769
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• AgBF4-catalyzed deoxygenative C2-amination of quinoline N-oxides with isothiocyanates

  2019cited by this paper
• Oxidative Coupling with S-N Bond Formation

  2018cited by this paper
• Recent advances in sulfur–nitrogen bond formation via cross-dehydrogenative coupling reactions

  2018cited by this paper
• Metal-free I2O5-mediated direct construction of sulfonamides from thiols and amines.

  2017cited by this paper
• An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation

  2017cited by this paper
• Electrochemical synthesis of sulfonamides from arenesulfonohydrazides or sodium p-methylbenzenesulfinate and amines

  2016cited by this paper
• I2/TBHP Mediated C-N and C-H Bond Cleavage of Tertiary Amines toward Selective Synthesis of Sulfonamides and β-Arylsulfonyl Enamines: The Solvent Effect on Reaction.

  2016cited by this paper
• Metal-free synthesis of sulfonamides via iodine-catalyzed oxidative coupling of sulfonyl hydrazides and amines

  2016cited by this paper
• Synthesis of sulfonamides via copper-catalyzed oxidative C-N bond cleavage of tertiary amines.

  2016cited by this paper
• Iodine-catalyzed N-sulfonylation of benzotriazoles with sodium sulfinates under mild conditions

  2016cited by this paper
• Iodine-catalyzed expeditious synthesis of sulfonamides from sulfonyl hydrazides and amines.

  2016cited by this paper
• A general iodine-mediated synthesis of primary sulfonamides from thiols and aqueous ammonia.

  2016cited by this paper
• Copper-catalyzed electrophilic amination of sodium sulfinates at room temperature.

  2015cited by this paper
• Synthesis of sulfonamides via I2-mediated reaction of sodium sulfinates with amines in an aqueous medium at room temperature

  2015cited by this paper
• Iodine catalysis: A green alternative to transition metals in organic chemistry and technology

  2015cited by this paper
• Substitution of alcohols by N-nucleophiles via transition metal-catalyzed dehydrogenation.

  2015cited by this paper
• Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature

  2015cited by this paper
• Metal‐Free Direct Construction of Sulfonamides via Iodine‐ Mediated Coupling Reaction of Sodium Sulfinates and Amines at Room Temperature

  2015cited by this paper
• Iodine‐Catalyzed Oxidative Amination of Sodium Sulfinates: A Convenient Approach to the Synthesis of Sulfonamides under Mild Conditions

  2015cited by this paper
• Copper-mediated S-N formation via an oxygen-activated radical process: a new synthesis method for sulfonamides.

  2014cited by this paper
• A powerful combination: recent achievements on using TBAI and TBHP as oxidation system.

  2014cited by this paper
• Copper-catalyzed Chan-Lam coupling between sulfonyl azides and boronic acids at room temperature.

  2014cited by this paper
• Direct approaches to nitriles via highly efficient nitrogenation strategy through C-H or C-C bond cleavage.

  2014cited by this paper
• Metal-free oxidative coupling of amines with sodium sulfinates: a mild access to sulfonamides

  2014cited by this paper
• Copper-catalyzed sulfonamides formation from sodium sulfinates and amines.

  2013cited by this paper
• Hypervalent Iodine Chemistry: Preparation, Structure, and Synthetic Applications of Polyvalent Iodine Compounds

  2013cited by this paper
• C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation.

  2012cited by this paper
• Ligand-free copper-catalyzed coupling of nitroarenes with arylboronic acids

  2012cited by this paper
• Cu(II)-catalyzed C-H (SP3) oxidation and C-N cleavage: base-switched methylenation and formylation using tetramethylethylenediamine as a carbon source.

  2012cited by this paper
• A green, mild and efficient one-pot method for the synthesis of sulfonamides from thiols and disulfides in water

  2012cited by this paper
• Regioselective and stereospecific cross-coupling of primary allylic amines with boronic acids and boronates through palladium-catalyzed C-N bond cleavage.

  2012cited by this paper
• Regioselective ring expansion of 2,4-diiminoazetidines via cleavage of C-N and C(sp3)-H bonds: efficient construction of 2,3-dihydropyrimidinesulfonamides.

  2012cited by this paper
• Catalytic asymmetric cleavage of sp3 C-N bonds for access to highly enantioenriched N-benzylic sulfonamides.

  2012cited by this paper
• Nitromethane with IBX/TBAF as a nitrosating agent: synthesis of nitrosamines from secondary or tertiary amines under mild conditions.

  2012cited by this paper
• Chan-Lam coupling reactions: synthesis of heterocycles

  2012cited by this paper
• C-N bond cleavage of allylic amines via hydrogen bond activation with alcohol solvents in Pd-catalyzed allylic alkylation of carbonyl compounds.

  2011cited by this paper
• Copper-catalyzed oxidative amination of benzoxazoles via C-H and C-N bond activation: a new strategy for using tertiary amines as nitrogen group sources.

  2011cited by this paper
• Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation.

  2011cited by this paper
• Sulfinamides as Highly Effective Amine Protecting Groups and Their Use in the Conversion of Amino Alcohols into Morpholines

  2011cited by this paper
• Synthesis and biological evaluation of some new 2-pyrazolines bearing benzene sulfonamide moiety as potential anti-inflammatory and anti-cancer agents.

  2011cited by this paper
• Design, synthesis, and X-ray crystallographic analysis of a novel class of HIV-1 protease inhibitors.

  2011cited by this paper
• Tunable stereoselective alkene synthesis by treatment of activated imines with nonstabilized phosphonium ylides.

  2011cited by this paper
• A general copper powder-catalyzed Ullmann-type reaction of 3-halo-4(1H)-quinolones with various nitrogen-containing nucleophiles.

  2011cited by this paper
• A general rhodium-catalyzed cyanation of aryl and alkenyl boronic acids.

  2011cited by this paper
• Mild Pd-catalyzed N-arylation of methanesulfonamide and related nucleophiles: avoiding potentially genotoxic reagents and byproducts.

  2011cited by this paper
• Enantioselective oxidation of C-O and C-N bonds using oxidases.

  2011cited by this paper
• Palladium-catalyzed carbonation-diketonization of terminal aromatic alkenes via carbon-nitrogen bond cleavage for the synthesis of 1,2-diketones.

  2011cited by this paper
• Mild and selective Ru-catalyzed formylation and Fe-catalyzed acylation of free (N-H) indoles using anilines as the carbonyl source.

  2011cited by this paper
• Copper‐Catalyzed Formation of Sulfur–Nitrogen Bonds by Dehydrocoupling of Thiols with Amines

  2010cited by this paper
• Catalytic regioselective synthesis of structurally diverse indene derivatives from N-benzylic sulfonamides and disubstituted alkynes.

  2010cited by this paper
• Copper-mediated N-heteroarylation of primary sulfonamides: synthesis of mono-N-heteroaryl sulfonamides.

  2010cited by this paper
• Synthesis and antimicrobial studies on novel sulfonamides containing 4-azidomethyl coumarin.

  2010cited by this paper
• Direct conversion of thiols and disulfides into sulfonamides

  2010cited by this paper
• A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with N-sulfonyl imines.

  2010cited by this paper
• Iron-catalyzed synthesis of glycine derivatives via carbon-nitrogen bond cleavage using diazoacetate.

  2010cited by this paper
• Activation of the C-N bond in nitromethane by palladium alpha-diimine complexes.

  2009cited by this paper
• Cleavage of C-N bonds in aniline derivatives on a ruthenium center and its relevance to catalytic C-C bond formation.

  2009cited by this paper
• Catalytic, PMe3-mediated conversion of secondary nitroalkanes to ketones: a very mild Nef-type process

  2008cited by this paper
• Reaction of [sigma:eta(5)-(C(9)H(6))C(2)B(9)H(10)]Zr(NMe(2))(DME) with guanidines: metallacarborane-mediated C-N bond cleavage and 1,5-sigmatropic rearrangement.

  2007cited by this paper
• Synthesis and anticonvulsant activity of sulfonamide derivatives-hydrophobic domain.

  2007cited by this paper
• Ruthenium-catalyzed carbon-carbon bond formation via the cleavage of an unreactive aryl carbon-nitrogen bond in aniline derivatives with organoboronates.

  2007cited by this paper
• A general ruthenium-catalyzed synthesis of aromatic amines.

  2007cited by this paper
• C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents.

  2007cited by this paper
• β‐Cyclodextrin‐Catalyzed Monosulfonylation of Amines and Amino Acids in Water

  2007cited by this paper
• Photoinduced C-N bond cleavage in 2-azido-1,3-diphenyl-propan-1-one derivatives: photorelease of hydrazoic acid.

  2007cited by this paper
• Expedient synthesis of sulfinamides from sulfonyl chlorides.

  2007cited by this paper
• Diazonium salts as substrates in palladium-catalyzed cross-coupling reactions.

  2006cited by this paper
• Photochemistry of 2-(1-naphthyl)-2H-azirines in matrixes and in solutions: wavelength-dependent C-C and C-N bond cleavage of the azirine ring.

  2005cited by this paper
• Intermolecular C-N addition of amides and S-N addition of sulfinamides to arynes.

  2005cited by this paper
• Sulfonamide drugs binding to the colchicine site of tubulin: thermodynamic analysis of the drug-tubulin interactions by isothermal titration calorimetry.

  2005cited by this paper
• Azoles as Suzuki cross-coupling leaving groups: syntheses of 6-arylpurine 2'-deoxynucleosides and nucleosides from 6-(imidazol-1-yl)- and 6-(1,2,4-triazol-4-yl)purine derivatives.

  2005cited by this paper
• Azoles as Suzuki Cross-Coupling Leaving Groups: Syntheses of 6-Arylpurine 2‘-Deoxynucleosides and Nucleosides from 6-(Imidazol-1-yl)- and 6-(1,2,4-Triazol-4-yl)purine Derivatives1

  2004cited by this paper
• Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction)

  2004cited by this paper
• Protease inhibitors of the sulfonamide type: Anticancer, antiinflammatory, and antiviral agents

  2003cited by this paper
• Bond dissociation energies of organic molecules.

  2003cited by this paper
• Copper-catalyzed N-arylation of sulfonamides with aryl bromides and iodides using microwave heating

  2003cited by this paper
• The first Suzuki cross-couplings of aryltrimethylammonium salts.

  2003cited by this paper
• Anticancer and antiviral sulfonamides.

  2003cited by this paper
• Palladium-catalyzed intermolecular coupling of aryl chlorides and sulfonamides under microwave irradiation.

  2003cited by this paper
• Carbonic anhydrase inhibitors: anticonvulsant sulfonamides incorporating valproyl and other lipophilic moieties.

  2002cited by this paper
• Pyrazolopyrimidine-2,4-dione sulfonamides: novel and selective calcitonin inducers.

  2002cited by this paper
• Pd-catalyzed intermolecular amidation of aryl halides: the discovery that xantphos can be trans-chelating in a palladium complex.

  2002cited by this paper
• A novel kind of antitumour drugs using sulfonamide as parent compound.

  2001cited by this paper
• Unusual molybdenum mediated C–N bond activation

  2001cited by this paper
• Palladium-catalyzed intermolecular coupling of aryl halides and amides.

  2000cited by this paper
• Neighbouring group assisted sulfonamide cleavage of Sharpless aminols under acetonation conditions

  1998cited by this paper
• Carbon−Heteroatom Bond-Forming Reductive Eliminations of Amines, Ethers, and Sulfides

  1998cited by this paper
• Pyridine CN Bond Cleavage Mediated by (silox)3Nb (silox = tBu3SiO)

  1997cited by this paper
• Arylamine C−N Bond Oxidative Addition to (silox)3Ta (silox = tBu3SiO)

  1996cited by this paper
• Comprehensive medicinal chemistry : the rational design, mechanistic study & therapeutic application of chemical compounds

  1990cited by this paper
• Polarized emission spectroscopy of photodissociating nitromethane at 200 and 218 nm

  1990cited by this paper
• Synthesis of sulfur-substituted phospholipid analogs as mechanistic probes of phospholipase A2 catalysis

  1989cited by this paper
• A MILD OXIDATIVE NEF REACTION

  1984cited by this paper
• Comprehensive organic chemistry : the synthesis and reactions of organic compounds

  1978cited by this paper

• Three-component synthesis of β-sulfonyl enamines and dienamines enabled by silver(i) acetate

  2025cites this paper
• Fabrication of an amino-modified MWCNTs grafted with chlorosulfonated PMIA nanofibrous membrane via electrospinning for efficient high-temperature dust filtration

  2023cites this paper
• Microwave assisted, Cu-catalyzed synthesis of sulfonamides using sodium sulfinates and amines

  2023cites this paper
• An Efficient Method for the Preparation of Sulfonamides from Sodium Sulfinates and Amines

  2022cites this paper
• Recent advances of sodium sulfinates in radical reactions

  2021cites this paper
• Iodine‐Catalyzed or ‐Mediated Reactions in Aqueous Medium

  2021cites this paper
• Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

  2021cites this paper
• Sulfonyl radical-induced regioselective cyclization of 3-aza-1,5-enynes with sulfonyl chlorides to produce 1,2-dihydropyridines by copper catalysis

  2021cites this paper
• Chiral Near-Infrared Fluorophores by Self-Promoted Oxidative Coupling of Cationic Helicenes with Amines / Enamines.

  2021cites this paper
• Electrosynthesis of S-thiocarbamates with disulfides as a sulfur source.

  2021cites this paper
• Formation of the Tertiary Sulfonamide C(sp3)-N Bond Using Alkyl Boronic Ester via Intramolecular and Intermolecular Copper-Catalyzed Oxidative Cross-Coupling.

  2021cites this paper
• Visible-light-initiated regioselective sulfonylation/cyclization of 1,6-enynes under photocatalyst- and additive-free conditions

  2020cites this paper
• Simple and sensitive detection of acrylamide based on hemoglobin immobilization in carbon ionic liquid paste electrode

  2020cites this paper
• Air-stable binuclear Titanium(IV) salophen perfluorobutanesulfonate with zinc power catalytic system and its application to C–S and C–Se bond formation

  2020cites this paper
• The clean preparation of multisubstituted pyrroles under metal- and solvent-free conditions

  2020cites this paper
• Direct cyanation, hydrocyanation, dicyanation and cyanofunctionalization of alkynes

  2020cites this paper
• I2-Catalyzed Aerobic α,β-Dehydrogenation and Deamination of Tertiary Alkylamines: Highly Selective Synthesis of Polysubstituted Pyrimidines via Hidden Acyclic Enamines.

  2020cites this paper
• Black TiO2 nanoparticles with efficient photocatalytic activity under visible light at low temperature: regioselective C–N bond cleavage toward the synthesis of thioureas, sulfonamides, and propargylamines

  2020cites this paper
• β-Selective Cu(II)-Catalyzed Dehydrogenative Enamination of Alkylbenzenes.

  2020cites this paper
• Ligand-Free, Quinoline N-Assisted Copper-Catalyzed Nitrene Transfer Reaction To Synthesize 8-Quinolylsulfimides.

  2019cites this paper
• Ag2CO3-mediated direct functionalization of alkyl nitriles: Facile synthesis of γ-ketonitriles through nitrile alkylation of enol acetates

  2019cites this paper
• Ultrasound accelerated synthesis of O-alkylated hydroximides under solvent- and metal-free conditions.

  2019cites this paper
• Visible-light-induced cascade sulfonylation/cyclization of N-propargylindoles with aryldiazonium tetrafluoroborates via the insertion of sulfur dioxide.

  2019cites this paper
• The concept of dual roles design in clean organic preparation

  2019cites this paper
• Visible-light-induced deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acids for the synthesis of 2-sulfonylquinoline via radical reactions

  2019cites this paper
• Silver-Promoted Decarboxylative Sulfonylation of Aromatic Carboxylic Acids with Sodium Sulfinates.

  2019cites this paper
• Regioselective Single-Electron Tsuji-Trost Reaction of Allylic Alcohols: A Photoredox/Nickel Dual Catalytic Approach.

  2019cites this paper
• Clean preparation of S-thiocarbamates with in situ generated hydroxide in 2-methyltetrahydrofuran

  2019cites this paper
• One‐Pot Synthesis of N ‐Substituted Enaminones from Ketones, Aromatic Nitriles and Halides

  2019cites this paper
• Aerobic α,β-C(sp3)-H Bond Difunctionalization and C-N Bond Cleavage of Triethylamine: Difunctional Ammonium Iodide Enabling the Regioselective Synthesis of 4-Arylpyrimido[1,2-b]indazoles.

  2019cites this paper
• Sustainable routes for quantitative green selenocyanation of activated alkynes

  2019cites this paper
• DESs: Green solvents for transition metal catalyzed organic reactions

  2019cites this paper
• Iodine-catalyzed sulfonylation of sulfonyl hydrazides with tert-amines: a green and efficient protocol for the synthesis of sulfonamides

  2019cites this paper