Highly efficient synthesis of substituted benzenes in the presence of B(HSO4)3 as a new and reusable catalyst under solvent-free conditions

Synthetic Communications

Volumn 43, Issue 16, 2013, Pages 2178-2190

  Safaei, Hamid Reza ^a   Davoodi, Mansooreh ^a   Shekouhy, Mohsen ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

B(HSO4)3; Cyclotrimerization reaction; Self condensation reactions; Solid acid; Solvent free reaction; Substituted benzenes

Indexed keywords

BENZENE DERIVATIVE; BORON; SULFONIC ACID DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; DRUG SYNTHESIS; POLYMERIZATION; RECYCLING;

EID: 84879123217     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2012.696300     Document Type: Article

References (61)

1. Clark, J. H. Solid acids for green chemistry. Acc. Chem. Res. 2002, 35, 791-797.
2. Ogawa, H.; Koh, T.; Taya, K.; Chihara, T. Catalysis at the toluene=water interface: Octadecyl immobilized H-ZSM-5 catalyst promoted hydrolysis of water-insoluble esters. J. Catal. 1994, 148, 493-500.
3. Harmer, M. A.; Farneth, W. E.; Sun, Q. High surface area nafion resin=silica nanocomposites: A new class of solid acid catalyst. J. Am. Chem. Soc. 1996, 118, 7708-7715.
4. Harmer, M. A.; Sun, Q. Solid acid catalysis using ion-exchange resins. Appl. Catal. A 2001, 221, 45-62.
5. Okuhara, T. Water-tolerant solid acid catalysts. Chem. Rev. 2002, 102, 3641-3666.
6. Ma, J.; Ng, S.; Yong, Y.; Luo, X.-Z.; Wang, X.; Liu, X.-W. Recyclable sulfonated amorphous carbon catalyzed Friedel-Crafts alkylation of indoles with,-unsaturated carbonyl compounds in water. Chem. Asian J. 2010, 5, 778-782.
7. Zong, M.-H.; Duan, Z.-Q.; Lou, W.-Y.; Smith, T. J.; Wu, H. Preparation of a sugar catalyst and its use for highly efficient production of biodiesel. Green Chem. 2007, 9, 434-437
8. Toda, M.; Takagaki, A.; Okamura, M.; Kondo, J. N.; Hayashi, S.; Domen, K.; Hara, M. Biodiesel made with sugar catalyst. Nature 2005, 438, 178-178.
9. 4)3: A novel and efficient solid acid catalyst for the regioselective conversion of epoxides to thiocyanohydrins under solvent-free conditions. J. Braz. Chem. Soc. 2008, 19, 1595-1599.
10. Kottas, G. S.; Clarke, L. I.; Horinek, D.; Michl, J. Artificial molecular rotors. Chem. Rev. 2005, 105, 1281-1376
11. Tour, J. M. Conjugated macromolecules of precise length and constitution: Organic synthesis for the construction of nanoarchitectures. Chem. Rev. 1996, 96, 537-553
12. Tour, J. M. In Stimulating Concepts in Chemistry; F. Vögtle, J. F. Stoddart, M. Shibasaki (Eds.); Wiley-VCH: Weinheim, 2000; pp. 237-253.
13. Trujillo, J. M.; Jorge, R. E.; Navarro, E.; Boada, J. Lignans from Justicia hyssopifolia. Phytochemistry 1990, 29, 2991-2993
14. Tsuji, K.; Nakamura, K.; Ogino, T.; Konishi, N.; Tojo, T.; Ochi, T.; Seki, N.; Matsuo, M. Synthesis and pharmacological properties of 2,3-diarylthiophenes. Chem. Pharm. Bull. 1998, 46, 279-286
15. Becker, F. F.; Mukhopadhyay, C.; Hackfeld, L.; Banik, I.; Banik, B. K. Synthesis and biological evaluation of dibenzofluorene derivatives. Bioorg. Med. Chem. 2000, 8, 2693-2699.
16. Watson, M. D.; Fechtenkotter, A.; Mullen, K. Big is beautiful- "Aromaticity" revisited from the viewpoint of macromolecular and supramolecular benzene chemistry. Chem. Rev. 2001, 101, 1267-1300, and references cited therein.
17. Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons; Wiley-VCH: Weinheim, 2001; p. 1.
18. Ebert, M.; Jungbauer, D. A.; Kleppinger, R.; Wendorff, J. H.; Kohne, B.; Praefcke, K. Structural and dynamic properties of a new type of discotic nematic compounds. Liq. Cryst. 1989, 4, 53-67.
19. Schneider, D. J.; Landis, D. A.; Fleitz, P. A.; Seliskar, C. J.; Kaufman, J. M.; Steppel, R. N. Characterization of new excimer pumped UV laser-dyes: p-Terphenyls. Laser Chem. 1991, 11, 49-62.
20. Roncali, J. Conjugated poly(thiophenes): Synthesis, functionalization, and applications. Chem. Rev. 1992, 92, 711-738
21. Akcelrud, L. Electroluminescent polymers. Prog. Polym. Sci. 2003, 28, 875-962.
22. Berresheim, A. J.; Muller, M.; Mullen, K. Polyphenylene Nanostructures. Chem. Rev. 1999, 99, 1747-1785
23. Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Polyethynylated cyclic π-systems: Scaffoldings for novel two-and three-dimensional carbon networks. Chem. Soc. Rev. 1999, 28, 107-119.
24. Williams, D. H.; Bardsley, B. The vancomycin group of antibiotics and the fight against resistant bacteria. Angew. Chem., Int. Ed. 1999, 38, 1172-1193
25. Nicolaou, K. C.; Boddy, C. N. C.; Brase, S.; Winssinger, N. The chemistry, biology, and medicine of the glycopeptide antibiotics. Angew. Chem., Int. Ed. 1999, 38, 2096-2152
26. Singh, F. V.; Kumar, A.; Goel, A. Synthesis of o, m-cymene-cored biaryls through a carbanion-induced ring transformation strategy. Tetrahedron Lett. 2006, 47, 7767-7770.
27. Goel, A.; Dixit, M.; Chaurasia, S.; Kumar, A.; Raghunandan, R.; Maulik, P. R.; Anand, R. S. Vapor-phase processable novel nonplanar donor-acceptor quateraryls for blue OLEDs. Org. Lett. 2008, 10, 2553-2556.
28. Yong, L.; Butenschon, H. The first cobalt catalyzed [2+2+2] alkyne cyclotrimerization in aqueous medium at room temperature. Chem. Commun. 2002, 2852-2853
29. Hilt, G.; Vogler, T.; Hess, W.; Galbiati, F. A simple cobalt catalyst system for the efficient and regioselective cyclotrimerisation of alkynes. Chem. Commun. 2005, 1474-1475
30. Conte, V.; Elakkari, E.; Floris, B.; Mirruzzo, V.; Tagliatesta, P. The cyclooligomerization of arylethynes in ionic liquids catalysed by ruthenium porphyrins: A case of real catalyst recycling. Chem. Commun. 2005, 1587-1588.
31. Pena, M. A.; Perez, I.; Sestelo, J. P.; Sarandeses, L. A. Multifold and sequential cross-coupling reactions with indium organometallics. Chem. Commun. 2002, 2246-2247
32. Bonvallet, P. A.; Breitkreuz, C. J.; Kim, Y. S.; Todd, E. M.; Traynor, K.; Fry, C. G.; Ediger, M. D.; McMahon, R. J. Organic Glass-Forming Materials: 1,3,5-Tris (naphthyl) benzene Derivatives. J. Org. Chem. 2007, 72, 10051-10057.
33. Hopff, H.; Schweizer, H. R.; Ghertsos, A.; Heer, A.; Solarsky, A. Chimia 1958, 12, 143-146.
34. Terai, H.; Takaya, H.; Naota, T. Rhodium-catalyzed direct aldol condensation of ketones: A facile synthesis of fused aromatic compounds. Tetrahedron Lett. 2006, 47, 1705-1708.
35. Dehmlow, E. V.; Kelle, T. Synthesis of new truxene derivatives: Possible precursors of fullerene partial structures. Synth. Commun. 1997, 27, 2021-2031
36. Lyle, R. E.; DeWitt, E. J.; Nichols, N. M.; Cleland, W. Acid-catalyzed condensations, I: 1,3,5-Triarylbenzenes. J. Am. Chem. Soc. 1953, 75, 5959-5961.
37. Lefeave, R. J. W. Reaction of hardwood lignin with hydrogen. J. Chem. Soc. 1938, 60, 1467-1471
38. Sampey, J. R. sym-Tritolylbenzene. J. Am. Chem. Soc. 1940, 62, 1953-1955.
39. Clapp, D.; Morton, A. The condensation of certain aromatic methyl ketones. J. Am. Chem. Soc. 1936, 58, 2172-2172.
40. Li, Z.; Sun, W.-H.; Jin, X.; Shao, C. Triple self-condensation of ketones yielding aromatics promoted with titanium tetrachloride. Synlett 2001, 1947-1949
41. Iranpoor, N.; Zeynizaded, B. TiCl3(OTf) catalyses the efficient conversion of acetophenones to 1,3,5-triaryl benzenes. Synlett 1998, 1079-1080
42. Volz, H.; Lecea, M. J. V. 1,3,5-Tris-(diphenyl-hexachloroantimonylmethyl) -benzol, ein stabiles Tricarboniumion. Tetrahedron Lett. 1966, 4683-4689
43. Lu, J.; Tao, Y.; D'iorio, M.; Li, Y.; Ding, J.; Day, M. Pure deep blue light-emitting diodes from alternating fluorene=carbazole copolymers by using suitable hole-blocking materials. Macromolecules 2004, 37, 2442-2449.
44. Elmorsy, S. S.; Pelter, A.; Smith, K.; Hursthouse, M. B.; Ando, D. Investigations of the tetrachlorosilane-ethanol-induced self-condensations of ketones. Tetrahedron Lett. 1992, 33, 821-824
45. Kotha, S.; Chakraborty, K.; Brahmachary E. A general and simple method for the synthesis of star-shaped thiophene derivatives. Synlett 1999, 10, 1621-1623
46. 3-symmetric nano-sized polyaromatic compounds by trimerization and Suzuki-Miyaura cross-coupling reactions. Eur. J. Org. Chem. 2004, 4003-4013
47. Dash, B. P.; Satapathy, R.; Aguire, J. A.; Hosmane, N. S. Synthesis of a new class of carborane-containing starshaped molecules via silicon tetrachloride-promoted cyclotrimerization reactions. Org. Lett. 2008, 10, 2247-2250.
48. 3. Synth. Commun. 1997, 27, 11-15.
49. Mahmoodi, N. O.; Hajati, N. Trisannelated benzene synthesis by copper(II) chloride. J. Chin. Chem. Soc. 2002, 49, 91-94.
50. Shirai, H.; Amano, N.; Hashimoto, Y.; Fukui, E.; Ishii, Y.; Ogawa, M. Trisannelated benzene synthesis by zirconium halide-catalyzed cyclodehydration of cycloalkanones. J. Org. Chem. 1991, 56, 2253-2256.
51. Zhang, G. P.; Qiu, R. H.; Xu, X. H.; Zhou, H. H.; Kuang, Y. F.; Chen, S. H. Zirconocene bis (perfluorooctanesulfonate) S-catalyzed high efficient synthesis of 1,3,5-Triaryl benzenes via cyclodehydration of ketones. Synth. Commun. 2012, 42, 858-864.
52. Jing, X.; Xu, F.; Zhu, Q.; Ren, X.; Yan, Ch.; Wang, L.; Wang, J. Novel method for the synthesis of 1,3,5-triarylbenzenes from ketones. Synth. Commun. 2005, 35, 3167-3171.
53. Zhao, Y.; Li, J.; Li, C.; Yin, K.; Yea, D.; Jia, X. PTSA-catalyzed green synthesis of 1,3,5-triarylbenzene under solvent-free conditions. Green Chem. 2010, 12, 1370-1372.
54. Ono, F.; Ishikura, Y.; Tada, Y.; Endo, M.; Sato, T. Efficient conversion of acetophenones into 1,3,5-Triarylbenzenes catalyzed by bismuth(III) trifluoromethanesulfonate tetrahydrate. Synlett 2008, 15, 2365-2367.
55. Zhang, S. L.; Xue, Z. F.; Gao, Y. R.; Mao, S.; Wang, Y. Q. Triple condensation of aryl methyl ketones catalyzed by amine and trifluoroacetic acid: Straightforward access to 1,3,5-triarylbenzenes under mild conditions. Tetrahedron Lett. 2012, 53, 2436-2439.
56. 6 ionic liquid. J. Chin. Chem. Soc. 2008, 55, 512-516.
57. Kumar, A.; Manish, D.; Singh, S. P.; Raghunandan, R.; Maulik, P. R., Goel, A. Reusable resin Amberlyst 15-catalyzed new convenient protocol for accessing arylated benzene scaffolds. Tetrahedron Lett. 2009, 50, 4335-4339.
58. Phatangare, K.; Padalkar, V.; Mhatre, D.; Patil, K.; Chaskar, A. Highly efficient and novel method for synthesis of 1,3,5-triarylbenzenes from acetophenones. Synth. Commun. 2009, 39, 4117-4121.
59. 2 as an efficient, mild, and heterogeneous catalytic system for the condensation of indoles with carbonyl compounds under solvent-free conditions. Arkivoc 2007, 14, 39-50.
60. n] as a new, efficient, and heterogeneous reagent for the synthesis of benzimidazole derivatives under microwave irradiation. Phosphorous, Sulfur Silicon Relat. Elem. 2009, 184, 147-155.
61. Salehi, P.; Zolfigol, M. A.; Shirini, F.; Baghbanzadeh, M. Silica sulfuric acid and silica chloride as efficient reagents for organic reactions. Curr. Org. Chem. 2006, 10, 2171-2189.