Thiocyanation of aromatic and heteroaromatic compounds using polymer-supported thiocyanate ion as the versatile reagent and ceric ammonium nitrate as the versatile single-electron oxidant

References

• Trahanovsky WS, Young LB. Controlled oxidation of organic compounds with cerium(IV). II. The oxidation of toluenes. J Org Chem. 1966;31:2033–2035. doi: 10.1021/jo01344a544
   Web of Science ®Google Scholar
• Ho TL. Ceric ion oxidation in organic chemistry. Synthesis. 1973;1973:347–354. doi: 10.1055/s-1973-22210
   Google Scholar
• Ho TL. Organic synthesis by oxidation with metal compounds. Plenum Press: New York; 1986.
   Google Scholar
• Nair V, Mathew J, Prabhakaran J. Carbon–carbon bond forming reactions mediated by cerium(IV) reagents. J Chem Soc Rev. 1997;26:127–132. doi: 10.1039/CS9972600127
   Web of Science ®Google Scholar
• Nair V, George TG, Nair LG, Panicker SB. A direct synthesis of aryl thiocyanates using cerium(IV) ammonium nitrate. Tetrahedron Lett. 1999;40:1195–1196. doi: 10.1016/S0040-4039(98)02563-5
   Web of Science ®Google Scholar
• Nair V, Deepthi A. Cerium(IV) ammonium nitrate: a versatile single-electron oxidant. Chem Rev. 2007;107:1862–1891. doi: 10.1021/cr068408n
   PubMed Web of Science ®Google Scholar
• Tamami B, Iranpoor N, Karimi Zarchi MA. Polymer-supported ceric(IV) catalyst: 1. Catalytic ring opening of epoxides. Polymer. 1993;34:2011–2013. doi: 10.1016/0032-3861(93)90457-L
   Web of Science ®Google Scholar
• Jiao J, Nguyen LX, Patterson DR, Flowers RA. An efficient and general approach to β-functionalized ketones. Org Lett. 2007;9:1323–1326. doi: 10.1021/ol070159h
   PubMed Web of Science ®Google Scholar
• Newman AA. Chemistry and biochemistry of thiocyanic acid and its derivatives. 1st ed. New York: Academic Press; 1975.
   Google Scholar
• Buchel KH. Chemie der pflanzen schutz-und schadlingsbe kampfungsmittle. Berlin: Springer; 1970.
   Google Scholar
• Gerson C, Sabater J, Scuri M, et al. The lactoperoxidase system functions in bacterial clearance of airways. Am J Respir Cell Mol Biol. 2000;22:665–671. doi: 10.1165/ajrcmb.22.6.3980
   PubMed Web of Science ®Google Scholar
• Akio M, Masaaki K. US Patent, 5, 155, 108, 1991. CA 114, 102028e (1991).
   Google Scholar
• Gorl U, Wolff S. DE, 4, 100, 217, 1992 (CA 117, 152581n, 1992).
   Google Scholar
• Batanero B, Barba F, Martín A. Preparation of 2,6-dimethyl-4-arylpyridine- 3,5-dicarbonitrile: a paired electrosynthesis. J Org Chem. 2002;67:2369–2371. doi: 10.1021/jo016065h
   PubMed Web of Science ®Google Scholar
• Kelly TR, Kim MH, Curtis AD. Structure correction and synthesis of the naturally occurring benzothiazinone BMY 40662. J Org Chem. 1993;58:5855–5857. doi: 10.1021/jo00073a057
   Web of Science ®Google Scholar
• Wood JL. Organic reactions Vol. 3. New York: Wiley; 1967.
   Google Scholar
• Leblanc BL, Jursic BC. Preparation of 5-alkylthio and 5-arylthiotetrazoles from thiocyanates using phase transfer catalysis. Synth Commun. 1998;28:3591–3599. doi: 10.1080/00397919808004905
   Web of Science ®Google Scholar
• Newman AA. Chemistry and biochemistry of thiocyanic acid and its derivatives. 1st ed. London: Academic Press; 1975.
   Google Scholar
• Billard T, Langlois BR, Medebielle M. Tetrakis(dimethylamino)ethylene (TDAE) mediated addition of difluoromethyl anions to heteroaryl thiocyanates. A new simple access to heteroaryl–SCF2R derivatives. Tetrahedron Lett. 2001;42:3463–3465. doi: 10.1016/S0040-4039(01)00514-7
   Web of Science ®Google Scholar
• Nguyen T, Rubinstein M, Wakselman C. Reaction of perfluoroalkyl carbanions with thiocyanates. Synthesis of fluorinated sulfides and sulfenyl chlorides. J Org Chem. 1981;46:1938–1940. doi: 10.1021/jo00322a047
   Web of Science ®Google Scholar
• Billard T, Large S, Langlois BR. Preparation of trifluoromethyl sulfides or selenides from trifluoromethyl trimethylsilane and thiocyanates or selenocyanates. Tetrahedron Lett. 1997;38:65–68. doi: 10.1016/S0040-4039(96)02216-2
   Web of Science ®Google Scholar
• Grieco PA, Yokoyama Y, Williams E. Aryl selenocyanates and aryl thiocyanates: reagents for the preparation of activated esters. J Org Chem. 1978;43:1283–1285. doi: 10.1021/jo00400a070
   Web of Science ®Google Scholar
• Zhang ZH, Liebeskind LS. Palladium-catalyzed, copper(I)-mediated coupling of boronic acids and benzylthiocyanate. A cyanide-free cyanation of boronic acids. Org Lett. 2006;8:4331–4333. doi: 10.1021/ol061741t
   PubMed Web of Science ®Google Scholar
• Riemschneider R, Wojahn F, Orlick G. Thiocarbamates. III.1 Aryl thiocarbamates from aryl thiocyanates. J Am Chem Soc. 1951;73:5905–5907. doi: 10.1021/ja01156a552
   Web of Science ®Google Scholar
• Riemschneider R. Thiocarbamates and related compounds. X. A new reaction of thiocyanates. J Am Chem Soc. 1956;78:844–847. doi: 10.1021/ja01585a038
   Web of Science ®Google Scholar
• Lee YT, Choi SY, Chung YK. Microwave-assisted palladium-catalyzed regioselective cyanothiolation of alkynes with thiocyanates. Tetrahedron Lett. 2007;48:5673–5677. doi: 10.1016/j.tetlet.2007.06.041
   Web of Science ®Google Scholar
• Toste FD, Stefano VD, Still IWJ. Thiocyanate as a versatile synthetic unit: Efficient conversion of ArSCN to aryl alkyl sulfides and aryl thioesters. Synth Commun. 1995;36:2949–2952.
   Google Scholar
• Grant MS, Snyder HR. Thiocyanation of indole. Some reactions of 3-thiocyanoindole. J Am Chem Soc. 1960;82:2742–2744. doi: 10.1021/ja01496a023
   Web of Science ®Google Scholar
• Toste FD, Stefano VD, Still IW. A versatile procedure for the preparation of aryl thiocyanates using N-thiocyanatosuccinimide (NTS). Synth Commun. 1995;25:1277–1286. doi: 10.1080/00397919508012691
   Web of Science ®Google Scholar
• Akhlaghinia B, Pourali AR, Rahmani M. Efficient and novel method for thiocyanation of aromatic compounds using trichloroisocyanuric acid/ammonium thiocyanate/Wet SiO2. Synth Commun. 2012;42:1184–1191. doi: 10.1080/00397911.2010.537424
   Web of Science ®Google Scholar
• Chakrabarty M, Sarkar S. A clay-mediated eco-friendly thiocyanation of indoles and carbazoles. Tetrahedron Lett. 2003;44:8131–8133. doi: 10.1016/j.tetlet.2003.09.032
   Web of Science ®Google Scholar
• Yadav JS, Reddy BVS, Shubashree S, Sadashiv K. Iodine/MeOH: a novel and efficient reagent system for thiocyanation of aromatics and heteroaromatics. Tetrahedron Lett. 2004;45:2951–2954. doi: 10.1016/j.tetlet.2004.02.073
   Web of Science ®Google Scholar
• Sajjadifar S. Green thiocyanation of aromatic and heteroaromatic compounds by using silica boron sulfonic acid as a new catalyst and H2O2 as mild oxidant. Am J Orga Chem. 2012;2:116–121. doi: 10.5923/j.ajoc.20120205.02
   Web of Science ®Google Scholar
• Jadhav VK, Pal RR, Wadgaonkar PP, Salunkhe MM. A facile synthesis of aryl thiocyanates using sodium perborate. Synth Commun. 2001;31:3041–3045. doi: 10.1081/SCC-100105678
   Web of Science ®Google Scholar
• Wu G, Liu Q, Shen Y, Wu W, Wu L. Regioselective thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and oxone. Tetrahedron Lett. 2005;46:5831–5834. doi: 10.1016/j.tetlet.2005.06.132
   Web of Science ®Google Scholar
• Iranpoor N, Firouzabadi H, Khalili D, Shahin R. A new application for diethyl azodicarboxylate: efficient and regioselective thiocyanation of aromatics amines. Tetrahedron Lett. 2010;51:3508–3510. doi: 10.1016/j.tetlet.2010.04.096
   Web of Science ®Google Scholar
• Iranpoor N, Firouzabadi H. A new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highly selective bromination, thiocyanation or isothiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers. Tetrahedron Lett. 2006;47:5531–5534. doi: 10.1016/j.tetlet.2006.05.145
   Web of Science ®Google Scholar
• Kumar A, Ahamd P, Maurya RA. Direct α-thiocyanation of carbonyl and β-dicarbonyl compounds using potassium peroxydisulfate–copper(II). Tetrahedron Lett. 2007;48:1399–1401. doi: 10.1016/j.tetlet.2006.12.103
   Web of Science ®Google Scholar
• Yadav JS, Reddy BVS, Krishna AD, Suresh Reddy Ch, Narsaiah AV. Ferric (III) chloride-promoted electrophilic thiocyanation of aromatic and heteroaromatic compounds. Synthesis. 2005;2:961–964. doi: 10.1055/s-2005-861852
   Web of Science ®Google Scholar
• Murthy Y, Govindh B, Diwakar B, Nagalakshmi K, Venu R. Microwave-assisted neat reaction technology for regioselective thiocyanation of substituted anilines and indoles in solid media. J Iran Chem Soc. 2011;8:292–297. doi: 10.1007/BF03246227
   Web of Science ®Google Scholar
• Pan XQ, Lei MY, Zou JP, Zhang W. Mn(OAc)3-promoted regioselective free radical thiocyanation of indoles and anilines. Tetrahedron Lett. 2009;50:347–349. doi: 10.1016/j.tetlet.2008.11.007
   Web of Science ®Google Scholar
• Memarian HR, Mohammadpoor-Baltork I, Nikoofar K. DDQ-promoted thiocyanation of aromatic and heteroaromatic compounds. Can J Chem. 2007;85:930–937. doi: 10.1139/v07-092
   Web of Science ®Google Scholar
• Wu J, Wu G, Wu L. Thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and I2O5. Synth Commun. 2008;38:2367–2373. doi: 10.1080/00397910802139254
   Web of Science ®Google Scholar
• Das B, Kumar BS. Efficient thiocyanation of indoles using para-toluene sulfonic acid. Synth Commun. 2010;40:337–341. doi: 10.1080/00397910902883744
   Web of Science ®Google Scholar
• Ley SV, Baxendale IR, Bream RN, et al. Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation. J Chem Soc Perkin Trans 1. 2000;3815–4195. doi: 10.1039/b006588i
   Google Scholar
• Sherrington DC, Hodge P. Synthesis and separation using functional polymers. New York: Wiley; 1988.
   Google Scholar
• Gallop MA, Barret RW, Dower WJ. Applications of combinatorial technologies to drug discovery. I. Background and peptide combinatorial libraries. J Med Chem. 1994;37:1233–1251. doi: 10.1021/jm00035a001
   PubMed Web of Science ®Google Scholar
• Merrifield RB. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J Am Chem Soc. 1963;85:2149–2154. doi: 10.1021/ja00897a025
   Web of Science ®Google Scholar
• Harrison CR, Hodge P. Polymer-supported reagents: the use of polymer-supported cyanide and thiocyanate to prepare nitriles, thiocyanates, and isothiocyanates. Synthesis. 1980;1980:299–301. doi: 10.1055/s-1980-28999
   Google Scholar
• Tamami B, Kiasat AR. Synthesis of thiiranes from oxiranes under mild and nonaqueous conditions using polymer supported thiocyanate. Synth Commun. 1996;26:3953–3958. doi: 10.1080/00397919608003817
   Web of Science ®Google Scholar
• Karimi Zarchi MA. Polymer-supported thiocyanate as new, versatile and efficient polymeric reagent for conversion of alkyl halides to corresponding alkyl thiocyanates under mild conditions. J Chin Chem Soc. 2007;54:1299–1302. doi: 10.1002/jccs.200700183
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Ebrahimi N. An efficient and simple method for diazotization-thiocyanation of aryl amine using cross-linked poly (4-Vinylpyridine) supported thiocyanate ion. Phosphorus Sulfur. 2012;187:1226–1235. doi: 10.1080/10426507.2012.681407
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Banihashemi R. An efficient and regioselective thiocyanation of aromatic and heteroaromatic compounds using cross-linked poly (4-vinylpyridine)-supported thiocyanate as a versatile reagent and potassium peroxydisulfate as a strong oxidizing agent. J Sulfur Chem. 2014;35:458–469. doi: 10.1080/17415993.2014.917375
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Banihashemi R. Green and efficient method for thiocyanation of aromatic and heteroaromatic compounds using cross-linked poly (4-vinylpyridine) supported thiocyanate ion as versatile reagent and oxone as mild oxidant. Phosphorus Sulfur. 2014;189:1378–1390. doi: 10.1080/10426507.2013.865123
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Nabaei R, Barani S. Diazotization-azidation of amines in water by using cross-linked poly(4-vinylpyridine)-supported azide ion. J Appl Polym Sci. 2012;123:788–795. doi: 10.1002/app.34515
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Nabaei R. Solvent-free diazotization–azidation of aryl amine using a polymer-supported azide ion. J Appl Polym Sci. 2012;124:2362–2369. doi: 10.1002/app.35294
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Ebrahimi N. Diazotization-iodination of aromatic amines in water mediated by crosslinked poly(4-vinylpyridine) supported sodium nitrite. J Appl Polym Sci. 2011;121:2621–2625. doi: 10.1002/app.34004
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Ebrahimi N. Diazotization–cyanation of aromatic amines with crosslinked poly(4-vinylpyridine)-supported cyanide ions. J Appl Polym Sci. 2012;125:2163–2169. doi: 10.1002/app.36394
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Escandari Z. A mild and clean synthesis of alkyl azides from alkyl halides mediated by poly(4-vinylpyridine)-supported sodium azide under nonaqueous conditions. J Appl Polym Sci. 2011;121:1916–1920. doi: 10.1002/app.32856
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Nazem F. Using a polymer-supported azide ion in [2+3] cycloaddition reaction of azide ion with nitriles. J Appl Polym Sci. 2013;123:1977–1982. doi: 10.1002/app.34701
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Ebrahimi N. Facile and one-pot synthesis of aryl azides via diazotization of aromatic amine using cross-linked poly(4-vinylpyridine)-supported nitrite ion and azidation by a Sandmeyer-type reaction. Iran Polym J. 2012;21:591–599. doi: 10.1007/s13726-012-0063-9
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Nazem F. One-pot three-component synthesis of 1,4-disubstituted 1H-1,2,3-triazoles using green and recyclable cross-linked poly(4-vinylpyridine)-supported copper sulfate/sodium ascorbate in water/t-BuOH system. J Iran Chem Soc. 2014;11:1731–1742. doi: 10.1007/s13738-014-0446-2
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Tarabsaz A. Chinese J Polym Sci. A versatile and regioselective synthesis of vicinal azidoalcohols using cross-linked poly(4-vinylpyridine) supported azide ion under solvent-free conditions. Chinese J Polym Sci. 2013;31:1660–1669. doi: 10.1007/s10118-013-1362-0
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Barani S. Rapid and facile synthesis of acyl azides from acyl halides using a polymer-supported azide ion under heterogeneous conditions. Chinese J Polym Sci. 2013;31:1002–1010. doi: 10.1007/s10118-013-1290-z
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Tarabsaz A. Versatile and efficient method for synthesis of β-halohydrins via regioselective ring opening reaction of epoxides using cross-linked poly (4-vinylpyridine) supported HCl and HBr under solvent-free conditions. J Polym Res. 2013;20:208–216. doi: 10.1007/s10965-013-0208-3
   Web of Science ®Google Scholar
• Karimi Zarchi MA, Tabatabaei Bafghi A. Synthesis of alkyl thiocyanates from alcohols using a polymer-supported thiocyanate ion promoted by cyanuric chloride/dimethylformamide. J Sulfur Chem. 2015;189:403–412. doi: 10.1080/17415993.2015.1035273
   Web of Science ®Google Scholar
• Mahajan US, Akamanchi KG. Facile method for thiocyanation of activated arenes using iodic acid in combination with ammonium thiocyanate. Synth Commun. 2009;39:2674–2682. doi: 10.1080/00397910802663402
   Web of Science ®Google Scholar
• Gitkis A, Becker JY. Anodic thiocyanation of mono- and disubstituted aromatic compounds. Electrochim Acta. 2010;55:5854–5859. doi: 10.1016/j.electacta.2010.05.035
   Web of Science ®Google Scholar
• Turro NJ. Photochemistry of ketones adsorbed on porous silica. Tetrahedron Lett. 1987;43:1589–1616. doi: 10.1016/S0040-4020(01)90273-X
   Web of Science ®Google Scholar