Mesoporous sBa-15 silica catalyst functionalized with phenylsulfonic acid groups (SbA-15-ph-So₃h) as efficient nanocatalyst for chemoselective thioacetalization of carbonyl compounds

References

• Greene TW, Wuts PGM. Protective groups in organic synthesis. 3rd ed. NewYork, NY: Wiley; 1999.
   Google Scholar
• Greene TW. Protective groups in organic synthesis. NewYork, NY: Wiley; 1981.
   Google Scholar
• Yu H, Dong D, Ouyang Y, et al. Chemoselective thioacetalization with odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid as a 1,3-propanedithiol equivalent. Can J Chem. 2005;83:1741–1745. doi: 10.1139/v05-184
   Web of Science ®Google Scholar
• Battaglia L, Pinna F, Strukul G. Thioacetalization of aldehydes and ketones in the presence of hydroxo complexes of platinum(II): an example of Lewis acid catalytic activity. Can J Chem. 2001;79:621–625. doi: 10.1139/v01-067
   Web of Science ®Google Scholar
• Bulman Page PC, Prodger JC, Westwood D. Diastereoselectivity in the addition of Grignard reagents to ketones controlled by the 1,3-dithiane 1-oxide asymmetric building block. Tetrahedron Lett. 1993;49:10355–10368. doi: 10.1016/S0040-4020(01)80562-7
   Google Scholar
• Nakata T, Nagao S, Mori S, et al. Total synthesis of (+)-pederin. 1. Stereocontrolled synthesis of (+)-benzoylpedamide. Tetrahedron Lett. 1985;26:6461–6464. doi: 10.1016/S0040-4039(00)99027-0
   Web of Science ®Google Scholar
• Evans DV, Truesdale LK, Grimm KG, et al. Stereochemical consequences of hydrogen exchange as a result of tritium atom reactions on solid aliphatic amino acids. J Am Chem Soc. 1977;99:5009–5017. doi: 10.1021/ja00457a020
   Web of Science ®Google Scholar
• Ong BC. A simple and efficient method of thioacetal – and ketalization. Tetrahedron Lett. 1980;21:4225–4228. doi: 10.1016/S0040-4039(00)92868-5
   Web of Science ®Google Scholar
• Muthusamy S, Babu SA, Gunanathan C. Indium(III) chloride as an efficient, convenient catalyst for thioacetalization and its chemoselectivity. Tetrahedron Lett. 2001;42:359–362. doi: 10.1016/S0040-4039(00)01966-3
   Web of Science ®Google Scholar
• Mirjalili BF, Zolfigol MA. An efficient procedure for acetalization of carbonyl compounds with P2O5/SiO2. Phosphorus Sulfur Silicon Relat Elem. 2004;179:1397–1401. doi: 10.1080/10426500490463583
   Web of Science ®Google Scholar
• Gupta N, Goverdhan SL, Singh J. Acidic ionic liquid [bmim]HSO4: An efficient catalyst for acetalization and thioacetalization of carbonyl compounds and their subsequent deprotection. Catal Commun. 2007;8:1323–1328. doi: 10.1016/j.catcom.2006.11.030
   Web of Science ®Google Scholar
• Firouzabadi H, Iranpoor N, Karimi B. Lithium bromide-catalyzed highly chemoselective and efficient dithioacetalization of α,β-unsaturated and aromatic aldehydes under solvent-free conditions. Synthesis. 1999;1999:58–60. doi: 10.1055/s-1999-3679
   Google Scholar
• Khan TH, Mondal E, Sahu PR, et al. Nickel(II) chloride as an efficient and useful catalyst for chemoselective thioacetalization of aldehydes. Tetrahedron Lett. 2003;44:919–922. doi: 10.1016/S0040-4039(02)02771-5
   Web of Science ®Google Scholar
• Firouzabadi H, Iranpoor N, Hazarkhani H. Trichloroisocyanuric acid as a mild and efficient catalyst for thioacetalization and transthio-acetalization reactions. Synlett. 2001;2001:1641–1643. doi: 10.1055/s-2001-17451
   Google Scholar
• Kamal A, Chouhan G. Mild and efficient chemoselective protection of aldehydes as dithioacetals employing N-bromosuccinimide. Synlett. 2002;2002:474–476. doi: 10.1055/s-2002-20469
   Google Scholar
• Firouzabadi H, Iranpoor N, Hazarkhani H. Iodine catalyzes efficient and chemoselective thioacetalization of carbonyl functions, transthioacetalization of O,O- and S,O-acetals and acylals. J Org Chem. 2001;66:7527–7529. doi: 10.1021/jo015798z
   PubMed Web of Science ®Google Scholar
• Bez G, Gogoi D. A rapid and efficient method for 1,3-dithiolane synthesis. Tetrahedron Lett. 2006;47:5155–5157. doi: 10.1016/j.tetlet.2006.05.057
   Web of Science ®Google Scholar
• Kamble VT, Bandgar BP, Muley DB, et al. An expedient and efficient chemoselective protection of carbonyl compounds and transthioacetalization of O,O- and S,O-acetals catalyzed by HBF4-SiO2. J Mol Catal A Chem. 2007;268:70–75. doi: 10.1016/j.molcata.2006.12.001
   Web of Science ®Google Scholar
• De SK. Yttrium triflate as an efficient and useful catalyst for chemoselective protection of carbonyl compounds. Tetrahedron Lett. 2004;45:2339–2341. doi: 10.1016/j.tetlet.2004.01.106
   Web of Science ®Google Scholar
• De SK. Vanadyl triflate as an efficient and recyclable catalyst for chemoselective thioacetalization of aldehydes. J. Mol Catal A Chem. 2005;226:77–79. doi: 10.1016/j.molcata.2004.09.044
   Web of Science ®Google Scholar
• De SK. Scandium chloride-catalyzed chemoselective thioacetalization of aldehydes. Synthesis. 2004;6:828–830.
   Google Scholar
• Veisi H, Ghorbani-Vaghei R, Akbari Dadamahaleh S. Poly(N-bromobenzene-1,3- disulfonamide) and N,N,N,N-Tetrabromobenzene-1,3-disulfonamide as a mild and efficient catalyst for chemoselective thioacetalization of carbonyl functions and transthioacetalization reactions. J Heterocyclic Chem. 2011;48:699–705. doi: 10.1002/jhet.620
   Web of Science ®Google Scholar
• Veisi H, Amiri M, Hamidian AH, et al. 1,3-Dibromo-5,5- dimethylhydantoin (DBH) as a mild and efficient catalyst for chemoselective thioacetalization of carbonyl compounds and dethioacetalization under mild conditions. Phosphorus Sulfur Silicon. 2010;185:689–696. doi: 10.1080/10426500902917669
   Web of Science ®Google Scholar
• De SK. Cobalt(II)chloride catalyzed chemoselective thioacetalization of aldehydes. Tetrahedron Lett. 2004;45:1035–1036. doi: 10.1016/j.tetlet.2003.11.082
   Web of Science ®Google Scholar
• Kamal A, Chouhan G. Scandium triflate as a recyclable catalyst for chemoselective thioacetalization. Tetrahedron Lett. 2002;43:1347–1350. doi: 10.1016/S0040-4039(01)02378-4
   Web of Science ®Google Scholar
• Veisi H, Sedrpoushan A, Zolfigol MA, et al. Silica phenyl sulfonic acid as a solid acid heterogeneous catalyst for chemoselective thioacetalization of carbonyl compounds and dethioacetalization under mild conditions. J. Heterocyclic Chem. 2013;50:E204–E206. doi: 10.1002/jhet.1011
   Web of Science ®Google Scholar
• Karimi B, Khalkhali M. Silica functionalized sulfonic acid as a recyclable interphase catalyst for chemoselective thioacetalization of carbonyl compounds in water. J Mol Catal A Chem. 2007;271:75–79. doi: 10.1016/j.molcata.2007.02.018
   Web of Science ®Google Scholar
• Komatsu N, Uda M, Suzuki H. Bismuth(III) halides and sulfate as highly efficient catalyst for the sulfenylation of carbonyl and related compounds. Synlett. 1995;1995:984–986. doi: 10.1055/s-1995-5137
   Google Scholar
• Moghadam FM, Boeini HZ. N-Benzyl-DABCO-tribromide as an efficient and mild reagent for deprotection of dithioacetals. Synth Commun. 2006;36:1093–1096. doi: 10.1080/00397910500498952
   Web of Science ®Google Scholar
• Hajipour AR, Mallakpour SE. Solid state deprotection of acetals and thioacetals using benzyltriphenylphosphonium peroxymonosulfate. Molecules. 2002;7:674–680. doi: 10.3390/70800674
   Web of Science ®Google Scholar
• Veisi H, Sedrpoushan A, Faraji AR, et al. A mesoporous SBA-15 silica catalyst functionalized with phenylsulfonic acid groups (SBA-15-Ph-SO3H) as a novel hydrophobic nanoreactor solid acid catalyst for a one-pot three-component synthesis of 2H- indazolo[2,1-b]phthalazine-triones and triazolo[1,2-a]indazole-triones. RSC Adv. 2015;5:68523–68530. doi: 10.1039/C5RA04949K
   Web of Science ®Google Scholar
• Veisi H, Sedrpoushan A, Zolfigol MA, et al. Synthesis and application of silica phenyl sulfonic acid as a solid acid heterogeneous catalyst for one-pot synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles and bis(indolyl)methanes in water. J Heterocyclic Chem. 2011;48:1448–1454. doi: 10.1002/jhet.765
   Web of Science ®Google Scholar
• Veisi H, Sedrpoushan A, Maleki B, et al. Palladium immobilized on amidoximefunctionalized magnetic Fe3O4 nanoparticles: a highly stable and efficient magnetically recoverable nanocatalyst for Sonogashira coupling reaction. Appl Organomet Chem. 2015;29:834–839. doi: 10.1002/aoc.3390
   Web of Science ®Google Scholar
• Veisi H, Sedrpoushan A, Hemmati S. Palladium supported on diaminoglyoximefunctionalized Fe3O4 nanoparticles as a magnetically separable nanocatalyst in Heck coupling reaction. Appl Organomet Chem. 2015;29:825–828. doi: 10.1002/aoc.3375
   Web of Science ®Google Scholar
• Mohanazadeh F, Veisi H, Sedrpoushan A, et al. A very useful and mild method for the deoxygenation of sulfoxide to sulfide with silica bromide as heterogeneous promoter. J Sulfur Chem. 2014;35:7–13. doi: 10.1080/17415993.2013.801478
   Web of Science ®Google Scholar
• Mohanazadeh F, Zolfigol MA, Sedrpoushan A, et al. Synthesis of silica bromide as heterogeneous reagent and its application to conversion of alcohols to alkyl bromides. Lett Org Chem. 2012;9:598–603. doi: 10.2174/157017812802850285
   Web of Science ®Google Scholar