Iodine-catalyzed regioselective 2-sulfonylation of indoles with sodium sulfinates.

Iodine-catalyzed selective 2-arylsulfonyl indole formation from indoles and sodium sulfinates is disclosed. Various substituted 2-arylsulfonyl indoles were obtained in one pot in the absence of metal catalyst at room temperature under air.

[1]  B. Hayter,et al.  Palladium-Catalyzed Three-Component Diaryl Sulfone Synthesis Exploiting the Sulfur Dioxide Surrogate DABSO** , 2013, Angewandte Chemie.

[2]  G. Manolikakes,et al.  Arylation of lithium sulfinates with diaryliodonium salts: a direct and versatile access to arylsulfones. , 2013, Organic letters.

[3]  Dalip Kumar,et al.  A Metal-Free and Microwave-Assisted Efficient Synthesis of Diaryl Sulfones , 2013 .

[4]  Zhiyong Wu,et al.  Sulfonylation of quinoline N-oxides with aryl sulfonyl chlorides via copper-catalyzed C-H bonds activation. , 2013, Organic letters.

[5]  G. Manolikakes,et al.  Metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts. , 2013, Organic letters.

[6]  A. Naeimi,et al.  Aqueous heterogeneous oxygenation of hydrocarbons and sulfides catalyzed by recoverable magnetite nanoparticles coated with copper(II) phthalocyanine , 2012 .

[7]  F. Bărbuceanu,et al.  New heterocyclic compounds from 1,2,4-triazole and 1,3,4-thiadiazole class bearing diphenylsulfone moieties. Synthesis, characterization and antimicrobial activity evaluation. , 2012, European journal of medicinal chemistry.

[8]  G. Deng,et al.  Palladium‐Catalyzed Direct and Site‐Selective Desulfitative Arylation of Indoles with Sodium Sulfinates , 2012 .

[9]  Junmei Wang,et al.  General copper-catalyzed transformations of functional groups from arylboronic acids in water. , 2011, Chemistry.

[10]  B. Stokes,et al.  Rh2(II)-catalyzed nitro-group migration reactions: selective synthesis of 3-nitroindoles from β-nitro styryl azides. , 2011, Journal of the American Chemical Society.

[11]  H. Neumann,et al.  Novel C-H functionalization of arenes: palladium-catalyzed synthesis of diaryl sulfides. , 2011, Chemical communications.

[12]  K. Maloney,et al.  A practical, one-pot synthesis of sulfonylated pyridines. , 2011, Organic letters.

[13]  M. Parvez,et al.  Synthesis of indoles by conjugate addition and ligand-free copper-catalyzed intramolecular arylation of activated acetylenes with o-haloanilines. , 2010, Chemistry.

[14]  A. Malikzay,et al.  Expansion of SAR studies on triaryl bis sulfone cannabinoid CB2 receptor ligands. , 2010, Bioorganic & medicinal chemistry letters.

[15]  B. Sreedhar,et al.  Iron(III) Chloride‐Catalyzed Direct Sulfonylation of Alcohols with Sodium Arenesulfinates , 2010 .

[16]  Jian Sun,et al.  A Facile and Efficient Approach to N-Protected-β-Sulfinyl- enamines via C-Sulfinylation of Enamides and Enecarbamates , 2010 .

[17]  K. Bahrami,et al.  TAPC-promoted oxidation of sulfides and deoxygenation of sulfoxides. , 2010, The Journal of organic chemistry.

[18]  K. P. Boroujeni.  Polystyrene Supported Al(OTf)3: a Stable, Efficient, Selective, and Reusable Catalyst for Sulfonylation of Arenes with Sulfonic Acids , 2010 .

[19]  M. A. Yurovskaya,et al.  2- and 3-phenylsulfonylindoles – synthetic equivalents of unsubstituted indole in N-alkylation reactions , 2010 .

[20]  T. Ikemoto,et al.  Imide-catalyzed oxidation system: sulfides to sulfoxides and sulfones. , 2010, The Journal of organic chemistry.

[21]  J. Hartwig,et al.  Iridium-catalyzed, regio- and enantioselective allylic substitution with aromatic and aliphatic sulfinates. , 2010, Organic letters.

[22]  K. P. Boroujeni.  Sulfonylation of aromatic compounds with sulfonic acids using silica gel-supported AlCl3 as a heterogeneous Lewis acid catalyst , 2010 .

[23]  Zhangjie Shi,et al.  Introduction: CH Activation. , 2017, Chemical reviews.

[24]  P. Vogel,et al.  Desulfinylation of prop-2-enesulfinic acid: experimental results and mechanistic theoretical analysis. , 2009, Journal of the American Chemical Society.

[25]  S. Tian,et al.  Catalyst-free alkylation of sulfinic acids with sulfonamides via sp(3) C-N bond cleavage at room temperature. , 2009, Organic letters.

[26]  V. M. Dong,et al.  Palladium-catalyzed C-H bond functionalization with arylsulfonyl chlorides. , 2009, Journal of the American Chemical Society.

[27]  M. Dewhirst,et al.  Nucleophilic addition of organozinc reagents to 2-sulfonyl cyclic ethers: stereoselective synthesis of manassantins A and B. , 2009, Organic letters.

[28]  P. Bodine,et al.  Identification of diarylsulfone sulfonamides as secreted frizzled related protein-1 (sFRP-1) inhibitors. , 2008, Journal of medicinal chemistry.

[29]  A. L. Simplício,et al.  Selective and mild oxidation of sulfides to sulfoxides or sulfones using H2O2 and Cp′Mo(CO)3Cl as catalysts , 2008 .

[30]  K. Bahrami,et al.  Highly selective catalytic Friedel–Crafts sulfonylation of aromatic compounds using a FeCl3-based ionic liquid , 2008 .

[31]  A. Alizadeh,et al.  Rapid and mild sulfonylation of aromatic compounds with sulfonic acids via mixed anhydrides using Tf2O , 2007 .

[32]  R. Batey,et al.  Cross-coupling of organoboronic acids and sulfinate salts using catalytic copper(II) acetate and 1,10-phenanthroline: synthesis of aryl and alkenylsulfones , 2007 .

[33]  G. Olah,et al.  Chlorotrimethylsilane-nitrate salts as oxidants: direct oxidative conversion of thiols and disulfides to sulfonyl chlorides. , 2007, The Journal of organic chemistry.

[34]  K. Bahrami.  Selective Oxidation of Sulfides to Sulfoxides and Sulfones Using Hydrogen Peroxide (H2O2) in the Presence of Zirconium Tetrachloride. , 2006 .

[35]  M. Lasne,et al.  Oxidation of aromatic lithium thiolates into sulfinate salts: an attractive entry to aryl sulfones labeled with carbon-11. , 2006, The Journal of organic chemistry.

[36]  Sukbok Chang,et al.  WO3 nanoparticles on MCM-48 as a highly selective and versatile heterogeneous catalyst for the oxidation of olefins, sulfides, and cyclic ketones. , 2005, Organic letters.

[37]  G. Dyker.  Handbook of C–H Transformations , 2005 .

[38]  H. Miyamura,et al.  Highly active, immobilized ruthenium catalysts for oxidation of alcohols to aldehydes and ketones. Preparation and use in both batch and flow systems. , 2005, Journal of the American Chemical Society.

[39]  Wei Zhu,et al.  Synthesis of aryl sulfones via L-proline-promoted CuI-catalyzed coupling reaction of aryl halides with sulfinic acid salts. , 2005, The Journal of organic chemistry.

[40]  S. D. Samant,et al.  Fe-pillared bentonite—an efficient catalyst for sulfonylation of arenes using aryl and alkyl sulfonyl chlorides , 2004 .

[41]  B. Harrison,et al.  1-(2-Aminoethyl)-3-(arylsulfonyl)-1H-indoles as novel 5-HT6 receptor ligands. , 2004, Bioorganic & medicinal chemistry letters.

[42]  G. Fabrizi,et al.  Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts. , 2004, The Journal of organic chemistry.

[43]  Alan S. Goldman,et al.  Activation and functionalization of C-H bonds , 2004 .

[44]  B. Bandgar,et al.  Unsymmetrical diaryl sulfones through palladium-catalyzed coupling of aryl boronic acids and arylsulfonyl chlorides. , 2004, Organic letters.

[45]  Lian‐Hua Li,et al.  Antimony(V) Chloride-Benzyltriethylammonium Chloride Complex as an Efficient Catalyst for Friedel−Crafts Acylation Reactions , 2004 .

[46]  E. Vedejs,et al.  Synthesis of the aziridinomitosene skeleton by intramolecular Michael addition of alpha-lithioaziridines: an aromatic route featuring deuterium as a removable blocking group. , 2004, The Journal of organic chemistry.

[47]  B. Reddy,et al.  InBr3-catalyzed sulfonation of indoles: a facile synthesis of 3-sulfonyl indoles , 2003 .

[48]  G. Vassort,et al.  SR33805, a Ca2+ antagonist with length‐dependent Ca2+‐sensitizing properties in cardiac myocytes , 2003, British journal of pharmacology.

[49]  G. Fabrizi,et al.  An efficient palladium-catalyzed synthesis of unsymmetrical diaryl sulfones from aryl bromides/triflates and arenesulfinates , 2003 .

[50]  G. Fabrizi,et al.  Unsymmetrical diaryl sulfones through palladium-catalyzed coupling of aryl iodides and arenesulfinates. , 2002, Organic letters.

[51]  Jeremy M. Baskin,et al.  An efficient copper catalyst for the formation of sulfones from sulfinic acid salts and aryl iodides. , 2002, Organic letters.

[52]  M. Salunkhe,et al.  Friedel-Crafts sulfonylation in 1-butyl-3-methylimidazolium chloroaluminate ionic liquids. , 2001, The Journal of organic chemistry.

[53]  T. G. George,et al.  An efficient one-pot synthesis of vinyl sulphones via CAN mediated reaction of aryl sulphinates and alkenes ☆ , 2001 .

[54]  J. Desmurs,et al.  Acylation and related reactions under microwaves. 4. Sulfonylation reactions of aromatics. , 2001, The Journal of organic chemistry.

[55]  B. Bandgar,et al.  ZINC-MEDIATED FAST SULFONYLATION OF AROMATICS , 2001 .

[56]  C. Frost,et al.  Indium-Catalysed Aryl and Alkyl Sulfonylation of Aromatics , 2001 .

[57]  V. Singh,et al.  An efficient method for aromatic Friedel–Crafts alkylation, acylation, benzoylation, and sulfonylation reactions , 2001 .

[58]  G. Prakash,et al.  Nafion-H catalysed sulfonylation of aromatics with arene/alkenesulfonic acids for the preparation of sulfones1a. , 2001, Chemical communications.

[59]  Y. Pommier,et al.  Diarylsulfones, a novel class of human immunodeficiency virus type 1 integrase inhibitors , 1997, Antimicrobial agents and chemotherapy.

[60]  R. Silvestri,et al.  2-Sulfonyl-4-chloroanilino moiety: a potent pharmacophore for the anti-human immunodeficiency virus type 1 activity of pyrrolyl aryl sulfones. , 1996, Journal of medicinal chemistry.

[61]  J. Herbert,et al.  Effect of SR 33805 on arterial smooth muscle cell proliferation and neointima formation following vascular injury. , 1995, European journal of pharmacology.

[62]  W. Greenlee,et al.  5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase. , 1993, Journal of medicinal chemistry.

[63]  O. Weislow,et al.  Diarylsulfones, a new chemical class of nonnucleoside antiviral inhibitors of human immunodeficiency virus type 1 reverse transcriptase , 1993, Antimicrobial Agents and Chemotherapy.

[64]  J. Bergman,et al.  Efficient synthesis of 2-chloro-, 2-bromo-, and 2-iodoindole , 1992 .

[65]  P. Hamel,et al.  Acid-catalyzed isomerization of 3-indolyl sulfides to 2-indolyl sulfides: first synthesis of 3-unsubstituted 2-arylthioindoles. Evidence for a complex intermolecular process , 1992 .

[66]  G. Broggini,et al.  New evidence on the formation of 3‐acylindoles by reaction of N‐phenylnitrones with α,β‐acetylenic sulfones , 1991 .

[67]  A. Katritzky,et al.  Carbon Dioxide: A Reagent for the Protection of Nucleophilic Centres and the Simultaneous Activation of Alternative Locations to Electrophilic Attack. , 1986 .

[68]  M. Ueda,et al.  A New Synthesis of Diaryl Sulfones , 1984 .

[69]  B. M. Graybill.  Synthesis of aryl sulfones , 1967 .