An efficient heterogeneous catalyst (CuO@ARF) for on-water C-S coupling reaction: an application to the synthesis of phenothiazine structural scaffold

Procter DJ: The synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones. J Chem Soc Perkin Trans 2000, 1: 835–871. 10.1039/a901128e Liu L, Stelmach JE, Natarajan SR, Chen M-H, Singh SB, Schwartz CD, Fitzgerald CE, O'Keefe SJ, Zaller DM, Schmatz DM, Doherty JB: SAR of 3,4-dihydropyrido[3,2-d]pyrimidone p38 inhibitors. Bioorg Med Chem Lett 2003, 13: 3979–3982. 10.1016/j.bmcl.2003.08.059 Jones DN: 3. In Comprehensive Organic Chemistry, vol 3. Edited by: Barton DH, Ollis DW. Pergamon, New York; 1979. Kaldor SW, Kalish VJ, Davies JF II, Shetty BV, Fritz JE, Appelt K, Burgess JA, Campanal KM, Chirgadze NY, Clawson DK, Dressman BA, Hatch SD, Khalil DA, Kosa MB, Lubbehusen PP, Muesing MA, Patick AK, Reich SH, Su KS, Tatlock JH: Viracept (nelfinavir mesylate, AG1343): a potent, orally bioavailable inhibitor of HIV-1 protease. J Med Chem 1997, 40: 3979–3985. 10.1021/jm9704098 De Martino G, Edler MC, La Regina G, Cosuccia A, Barbera MC, Barrow D, Nicholson RI, Chiosis G, Brancale A, Hamel E, Artico M, Silvestri R: New arylthioindoles: potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies. J Med Chem 2006, 49: 947–954. 10.1021/jm050809s Liu G, Huth JR, Olejniczak ET, Mendoza F, Fesik SW, von Geldern TW: Novel p -arylthio cinnamides as antagonists of leukocyte function-associated antigen-1/intracellular adhesion molecule-1 interaction. 2. Mechanism of inhibition and structure-based improvement of pharmaceutical properties. J Med Chem 2001, 44: 1202–1210. 10.1021/jm000503f Nielsen SF, Nielsen EØ, Olsen GM, Liljefors T, Peters D: Novel potent ligands for the central nicotinic acetylcholine receptor: synthesis, receptor binding, and 3D-QSAR analysis. J Med Chem 2000, 43: 2217–2226. 10.1021/jm990973d Korth C, May BCH, Cohen FE, Prusiner SB: Acridine and phenothiazine derivatives as pharmacotherapeutics for prion disease. Proc Natl Acad Sci U S A 2001, 98: 9836–9841. 10.1073/pnas.161274798 Hickman RJS, Christie BJ, Guy RW, White T: Synthesis of aromatic S-substituted derivatives of N -acetyl-L-cysteine. Aust J Chem 1985, 38: 899–904. 10.1071/CH9850899 Khatik GL, Kumar R, Chakraborti AK: Catalyst-free conjugated addition of thiols to α, β-unsaturated carbonyl compounds in water. Org Lett 2006, 8: 2433–2436. 10.1021/ol060846t Migita T, Shimizu T, Asami Y, Shiobara J, Kato Y, Kosugi M: The palladium catalyzed nucleophilic substitution of aryl halides by thiolate anions. Bull Chem Soc Jpn 1980, 53: 1385–1389. 10.1246/bcsj.53.1385 Eichman CC, Stambuli JP: Transition metal catalyzed synthesis of aryl sulfides. Molecules 2011, 16: 590–608. 10.3390/molecules16010590 Guan P, Cao C, Liu Y, Li Y, He P, Chen Q, Liu G, Shi Y: Efficient nickel/N-heterocyclic carbene catalyzed C–S cross-coupling. Tetrahedron Lett 2012, 53: 5987–5992. 10.1016/j.tetlet.2012.08.055 Chen C-K, Chen Y-W, Lin C-H, Lin H-P, Lee C-F: Synthesis of CuO on mesoporous silica and its applications for coupling reactions of thiols with aryl iodides. Chem Commun 2010, 46: 282–284. 10.1039/b918117b Wong YC, Jayanth TT, Cheng CH: Cobalt-catalyzed aryl-sulfur bond formation. Org Lett 2006, 8: 5613–5616. 10.1021/ol062344l Correa A, Carril M, Bolm C: Iron-catalyzed S-arylation of thiols with aryl iodides. Angew Chem Int Ed 2008, 47: 2880–2883. 10.1002/anie.200705668 Lai CS, Kao HL, Wang YJ, Lee CF: A general rhodium-catalyzed cross-coupling reaction of thiols with aryl iodides. Tetrahedron Lett 2012, 53: 4365–4367. 10.1016/j.tetlet.2012.06.054 Liu T-J, Yi C-L, Chan C-C, Lee C-F: Manganese-catalyzed cross-coupling of thiols with aryl iodides. Chem Asian J 2013, 8: 1029–1034. 10.1002/asia.201300045 Reddy VP, Kumar AV, Swapna K, Rao KP: Nano indium oxide as a recyclable Catalyst for C-S cross-coupling of thiols with aryl halides under ligand free conditions. Org Lett 2009, 11: 1697–1700. 10.1021/ol900009a Hegedus LL, McCabe RW (1984) ᅟ. In: Catalysis Poisoning. Marcel Dekker, New York Chen YJ, Chen HH: 1,1,1-Tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols. Org Lett 2006, 8: 5609–5612. 10.1021/ol062339h Bates CG, Gujadhur RK, Venkataraman D: A general method for the formation of aryl-sulfur bonds using copper(I) catalysts. Org Lett 2002, 4: 2803–2806. 10.1021/ol0264105 Heiz U: Landman U Nanocatalysis. Springer–Verlag, Springer Berlin; 2007. Kamal A, Srinivasulu V, Murty JNSRC, Shankaraiah N, Nagesh N, Reddy TS, Rao AVS: Copper oxide NPs supported on graphene oxide- catalyzed S-arylation: an efficient and ligand-free synthesis of aryl sulfides. Adv Synth Catal 2013, 355: 2297–2307. 10.1002/adsc.201300416 Schwab RS, Singh D, Alberto EE, Piquini P, Rodrigues OED, Braga AL: C–S cross-coupling of thiols with aryl iodides under ligand-free conditions using nano copper oxide as a recyclable catalyst in ionic liquid. Catal Sci Technol 2011, 1: 569–573. 10.1039/c1cy00091h Rout L, Sen TK, Punniyamurthy T: Efficient CuO-nanoparticle-catalyzed C-S cross-coupling of thiols with iodobenzene. Angew Chem Int Ed 2007, 46: 5583–5586. 10.1002/anie.200701282 Rout L, Saha P, Jammi S, Punniyamurthy T (2008) Efficient copper(I)-catalyzed C–S cross coupling of thiols with aryl halides in water. Eur J Org Chem 2008ᅟ:640–643 Carril M, SanMartin R, Dominguez E, Tellitu I: Simple and efficient recyclable catalytic system for performing copper-catalysed S-arylation reactions in the presence of water. Chem Eur J 2007, 13: 5100–5105. 10.1002/chem.200601737 Malik P, Chakraborty D: Bi(III)-catalyzed C-S cross-coupling reaction. Appl Organomet Chem 2012, 26: 557–561. 10.1002/aoc.2871 Lan M-T, Wu W-Y, Huang S-H, Luo K-L, Tsai F-Y: Reusable and efficient CoCl 2 .6H 2 O/cationic 2,2′-bipyridyl system-catalyzed S-arylation of aryl halides with thiols in water under air. RSC Adv 2011, 1: 1751–1755. 10.1039/c1ra00406a Wu WY, Wang JC, Tsai FY: A reusable FeCl 3  · 6H 2 O/cationic 2,2′-bipyridyl catalytic system for the coupling of aryl iodides with thiols in water under aerobic conditions. Green Chem 2009, 11: 326–329. 10.1039/b820790a Basu B, Das S, Das P, Mandal B, Banerjee D, Almqvist F (2009) Palladium supported on a polyionic resin as an efficient, ligand-free, and recyclable catalyst for Heck, Suzuki-Miyaura, and Sonogashira reaction. Synthesis ᅟ:1137–1146 Sengupta D, Saha J, De G, Basu B: Pd/Cu bimetallic NPs embedded in macroporous ion-exchange resins: an excellent heterogeneous catalyst for the Sonogashira reaction. J Mater Chem A 2014, 2: 3986–3992. 10.1039/c3ta14916a Paul S, Basu B: Synthesis of libraries of quinoxalines through eco-friendly tandem oxidation–condensation or condensation reactions. Tetrahedron Lett 2011, 52: 6597–6602. 10.1016/j.tetlet.2011.09.141 Paul S, Basu B: Highly selective synthesis of libraries of 1,2-disubstituted benzimidazoles using silica gel soaked with ferric sulfate. Tetrahedron Lett 2012, 53: 4130–4133. 10.1016/j.tetlet.2012.05.129 Rhee H-W, Choi SJ, Yoo SH, Jang YO, Park HH, Pinto RM, Cameselle JC, Sandoval FJ, Roje S, Han K, Chung DS, Suh J, Hong J-I: A bifunctional molecule as an artificial flavin mononucleotide cyclase and a chemosensor for selective fluorescent detection of flavins. J Am Chem Soc 2009, 131: 10107–10112. 10.1021/ja9018012 Basu B, Bhuiyan MMH, Das P, Hossain I: Catalytic transfer reduction of conjugated alkenes and an imine using polymer-supported formates. Tetrahedron Lett 2003, 44: 8931–8934. 10.1016/j.tetlet.2003.10.019 Dar MA, Nam SH, Youn SK, Kim WB: Synthesis, characterization, and electrochemical properties of self-assembled leaf-like CuO nanostructures. J Solid State Electrochem 2010, 14: 1719–1726. 10.1007/s10008-010-1022-z Bahrami K, Khodaei MM, Nejati A: Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles. Green Chem 2010, 12: 1237–1241. 10.1039/c000047g Jammi S, Barua P, Rout L, Saha P, Punniyamurthy T: Efficient ligand-free nickel-catalyzed C–S cross-coupling of thiols with aryl iodides. Tetrahedron Lett 2008, 49: 1484–1487. 10.1016/j.tetlet.2007.12.118 Cramer CJ, Truhlar DG ACS (eds) (1994) Structure and Reactivity in Aqueous Solution. Washington, DC Sharma G, Kumar R, Chakraborti AK: ‘On water’ synthesis of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines catalysed by sodium dodecyl sulfate (SDS). Tetrahedron Lett 2008, 49: 4269–4271. 10.1016/j.tetlet.2008.04.146 Kumar D, Seth K, Kommi DN, Bhagat S, Chakraborti AK: Surfactant micelles as microreactors for the synthesis of quinoxalines in water: scope and limitations of surfactant catalysis. RSC Adv 2013, 3: 15157–15168. 10.1039/c3ra41038b Seth K, Roy SR, Pipaliya BV, Chakraborti AK: Synergistic dual activation catalysis by palladium nanoparticles for epoxide ring opening with phenols. Chem Commun 2013, 49: 5886–5888. and references cited therein 10.1039/c3cc42507j Jana S, Dutta B, Bera R, Koner S: Immobilization of palladium in mesoporous silica matrix: preparation, characterization, and its catalytic efficacy in carbon-carbon coupling reactions. Inorg Chem 2008, 47: 5512–5520. 10.1021/ic8004294 Ma D, Geng Q, Zhang H, Jiang Y: Assembly of substituted phenothiazines by a sequentially controlled CuI/l-proline-catalyzed cascade C–S and C–N bond formation. Angew Chem Int Ed 2010, 49: 1291–1294. 10.1002/anie.200905646