The use of polymeric sulfides as catalysts for the para-regioselective chlorination of phenol and 2-chlorophenol

References

• Ullmann’s encyclopedia of industrial chemistry. 6th ed. Weinheim: Wiley-VCH; 1998.
   Google Scholar
• Song Y. Insight into the mode of action of 2,4-dichlorophenoxyacetic acid (2,4-D) as an herbicide. J Integr Plant Biol. 2014;56:106–113. doi: 10.1111/jipb.12131
   PubMed Web of Science ®Google Scholar
• Peterson GE. The discovery and development of 2,4-D. Agricul His. 1967;41(3):243–254.
   Google Scholar
• Luther FB, Louis EB. Production of aromatic-oxyaliphatic carboxylates. United States Patent US 2,516,611. 1950.
   Google Scholar
• Nahide PD, Ramadoss V, Juárez-Ornelas KA, et al. In situ formed I(III)-based reagent for the electrophilic ortho-chlorination of phenols and phenol ethers: the use of PIFA-AlCl3 System. Eur J Org Chem. 2018;2018:485–493. doi: 10.1002/ejoc.201701399
   Google Scholar
• Xiong X, Yeung Y-Y. Ammonium salt-catalyzed highly practical ortho-selective monohalogenation and phenylselenation of phenols: scope and applications. ACS Catal. 2018;8:4033–4043. doi: 10.1021/acscatal.8b00327
   Web of Science ®Google Scholar
• Xin H, Yang S, An B, et al. Selective water-based oxychlorination of phenol with hydrogen peroxide catalysed by manganous sulfate. RSC Adv. 2017;7:13467–13472. doi: 10.1039/C7RA00319F
   Web of Science ®Google Scholar
• Maddox SM, Dinh AN, Armenta F, et al. A practical Lewis base catalyzed electrophilic chlorination of arenes and heterocycles. Org Lett. 2016;18:5476–5479. doi: 10.1021/acs.orglett.6b02650
   PubMed Web of Science ®Google Scholar
• Mu M, Snider BB. Syntheses of chloroisosulochrin and isosulochrin and biomimetic elaboration to maldoxin, maldoxone, dihydromaldoxin, and dechlorodihydromaldoxin. Org Lett. 2011;13:4224–4227. doi: 10.1021/ol201561w
   PubMed Web of Science ®Google Scholar
• Denmark SE, Beutner GL. Lewis base catalysis in organic synthesis. Angew Chem Int Ed Engl. 2008;47:1560–1638. doi: 10.1002/anie.200604943
   PubMed Web of Science ®Google Scholar
• Smith K, El-Hiti GA. Catalytic, green and regioselective Friedel-Crafts acylation of simple aromatics and heterocycles over zeolites. Curr Org Chem. 2015;19:585–598. doi: 10.2174/1385272819666150211002257
   Web of Science ®Google Scholar
• Smith K A, El-Hiti GA MH. Highly regioselective dinitration of toluene over zeolite Hβ. J Catal. 2013;297:244–247. doi: 10.1016/j.jcat.2012.10.017
   Web of Science ®Google Scholar
• Smith K, Al-Khalaf AKH, El-Hiti GA, et al. Highly regioselective di-tert-amylation of naphthalene over reusable HM zeolite catalyst. Green Chem. 2012;14:1103–1110. doi: 10.1039/c2gc16443d
   Web of Science ®Google Scholar
• Smith K, El-Hiti GA. Use of zeolites for green and para-selective electrophilic aromatic substitution reactions. Green Chem. 2011;13:1579–1608. doi: 10.1039/c0gc00689k
   Web of Science ®Google Scholar
• Smith K, Ewart GM, El-Hiti GA, et al. Study of regioselective methanesulfonylation of simple aromatics with methanesulfonic anhydride in the presence of zeolite catalysts. Org Biomol Chem. 2004;2:3150–3154. doi: 10.1039/b409922b
   PubMed Web of Science ®Google Scholar
• Smith K, El-Hiti GA, Butters M. Acetylation of aromatic ethers using acetic anhydride over solid acid catalysts in a solvent-free system. Scope of the reaction for substituted ethers. Org Biomol Chem. 2003;1:1560–1564. doi: 10.1039/b301260c
   PubMed Web of Science ®Google Scholar
• Smith K, Roberts SD, El-Hiti GA. Study of regioselective dialkylation of naphthalene in the presence of reusable zeolite catalysts. Org Biomol Chem. 2003;1:1552–1559. doi: 10.1039/b212775j
   PubMed Web of Science ®Google Scholar
• Smith K, El-Hiti GA, Bahzad D, et al. Highly efficient and selective electrophilic and free radical catalytic bromination reactions of simple aromatic compounds using bromine in the presence of reusable zeolites. J Chem Soc, Perkin Trans. 2000;1:2745–2752. doi: 10.1039/b002157l
   Google Scholar
• Smith K, Butters M, Paget WE, et al. Highly selective monochlorination of aromatic compounds under mild conditions by tert-butyl hypochlorite in the presence of zeolites. Green Chem. 1999;1:83–90. doi: 10.1039/a901395d
   Web of Science ®Google Scholar
• Smith K, Zhenhua Z, Hodgson PKG. Synthesis of aromatic ketones by acylation of aryl ethers with carboxylic anhydrides in the presence of zeolite H-β (H-BEA) in the absence of solvent. J Mol Catal A. 1998;134:121–128. doi: 10.1016/S1381-1169(98)00028-4
   Web of Science ®Google Scholar
• Smith K, Musson A, DeBoos GA. A novel method for the nitration of simple aromatic compounds. J Org Chem. 1998;63:8448–8454. doi: 10.1021/jo981557o
   Web of Science ®Google Scholar
• Smith K, Ewart GM, Randles KR. Regioselective methanesulfonylation of toluene catalysed by cation-exchanged zeolite beta. J Chem Soc, Perkin Trans. 1997;1:1085–1086. doi: 10.1039/a701025g
   Google Scholar
• DeLaude L, Laszlo P, Smith K. Heightened selectivity in aromatic substitutions by the use of solid supports and catalysts. Acc Chem Res. 1993;26:607–613. doi: 10.1021/ar00036a001
   Web of Science ®Google Scholar
• Smith K, James DM, Matthews I, et al. Selective para-bromination of phenols via a regenerable polymer-bound tetralkylammonium tribromide. J Chem Soc Perkin Trans. 1992;1:1877–1878. doi: 10.1039/p19920001877
   Google Scholar
• Smith K, Butters M, Nay B. Highly para-selective mono-chlorination of aromatic compounds under mild conditions by t-butyl hypochlorite in the presence of zeolites. Synthesis (Stuttgart). 1985(12): 1157–1158. doi: 10.1055/s-1985-31462
   Web of Science ®Google Scholar
• Gnaim JM, Sheldon RA. Shape-selective para-chlorination of phenol using sulfuryl chloride with the aid of microporous catalysts. Tetrahedron Lett. 2004;45:9397–9399. doi: 10.1016/j.tetlet.2004.10.109
   Web of Science ®Google Scholar
• Ratton S, Leblanc J-C. Process for the selective chlorination of phenolic compounds. European Patent, EP0,196,260, 1986.
   Google Scholar
• Ogata Y, Kimura M, Kondo Y, et al. Orientation in the chlorination of phenol and of anisole with sodium and t-butyl hypochlorites in various solvents. J Chem Soc. Perkin Trans. 1984;2:451–453. doi: 10.1039/p29840000451
   Google Scholar
• Watson WD. Regioselective para-chlorination of activated aromatic compounds. J Org Chem. 1985;50:2145–2148. doi: 10.1021/jo00212a029
   Web of Science ®Google Scholar
• Watson WD. Chlorination with sulfuryl chloride. United States Patent US 3,920,757A, 1975.
   Google Scholar
• Smith K, Tzimas M, Brown CM, et al. Dialkyl sulfides as selective catalysts for the chlorination of phenols. Sulfur Lett. 1999;22:89–101.
   Google Scholar
• Tzimas M, Smith K, Brown C, et al. Chlorination of aromatic compounds and catalysts therefor. European Patent EP0866049A2, 1998.
   Google Scholar
• Smith K, Al-Zuhairi AJ, El-Hiti GA, et al. Comparison of cyclic and polymeric disulfides as catalysts for the regioselective chlorination of phenols. J Sulfur Chem. 2015;36:74–85. doi: 10.1080/17415993.2014.965170
   Web of Science ®Google Scholar
• Smith K, Williams D, El-Hiti GA. Regioselective chlorination of phenols in the presence of tetrahydrothiopyran derivatives. J Sulfur Chem. 2019;40:529–538. doi: 10.1080/17415993.2019.1620230
   Web of Science ®Google Scholar
• Smith K, Tzimas M, Brown CM, et al. Dithiaalkanes and modified Merrifield resins as selective catalysts for the chlorination of phenols. Sulfur Lett. 1999;22:103–123.
   Google Scholar
• Tzimas M, Smith K, Brown C, et al. Chlorination of aromatic compounds and catalysts therefor. European Patent EP0866048A2, 1998.
   Google Scholar
• Smith K, Al-Zuhairi AJ, Elliott MC, et al. Regioselective synthesis of important chlorophenols in the presence of methylthioalkanes with remote SMe, OMe or OH substituents. J Sulfur Chem. 2018;39:607–621. doi: 10.1080/17415993.2018.1493111
   Web of Science ®Google Scholar
• Smith K, El-Hiti GA, Al-Zuhairi AJ. The synthesis of polymeric sulfides by reaction of dihaloalkanes with sodium sulfide. J Sulfur Chem. 2011;32:521–531. doi: 10.1080/17415993.2011.616589
   Web of Science ®Google Scholar
• Smith K, Balakit AA, El-Hiti GA. Poly(propylene sulfide)–borane: reagent for organic synthesis. Tetrahedron. 2012;68:7834–7839. doi: 10.1016/j.tet.2012.07.037
   Web of Science ®Google Scholar
• Smith K, Balakit AA, Pardasani RT, et al. New polymeric sulfide–borane complexes: convenient hydroborating and reducing reagents. J Sulfur Chem. 2011;32:282–295.
   Web of Science ®Google Scholar