Taming of superacids: PVP-triflic acid as an effective solid triflic acid equivalent for Friedel-Crafts hydroxyalkylation and acylation

Journal of Fluorine Chemistry

Volumn 171, Issue , 2015, Pages 102-112

  Prakash, G K Surya ^a   Paknia, Farzaneh ^a   Kulkarni, Aditya ^a   Narayanan, Arjun ^a   Wang, Fang ^a   Rasul, Golam ^a   Mathew, Thomas ^a   Olah, George A ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

Acylation; Hydroxyalkylation; PVP:triflic acid; Solid superacid; Trifluoromethanesulfonic acid

Indexed keywords

EID: 84923071884     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2014.08.020     Document Type: Article

References (95)

1. G.A. Olah Friedel-Crafts and Related Reactions, vol. 2 Part I Ed. 1964 John Wiley & Sons New York, NY
2. G.A. Olah Friedel-Crafts Chemistry 1973 Wiley Interscience New York, NY
3. G. Sartori, and R. Maggi Chem. Rev. 106 2006 1077 1104
4. I.V. Kozhevnikov Appl. Catal., A: Gen. 256 2003 3 18
5. T. Okayasu, K. Saito, H. Nishide, and M.T.W. Hearn Green Chem. 12 2010 1981 1989
6. S.K. Jana Catal. Surv. Asia 2 2006 98 109
7. K. Omata Appl. Catal., A: Gen. 407 2011 112 117
8. K.-I. Shimizua, and A. Satsumav Energy Environ. Sci. 4 2011 3140 3153
9. G.A. Olah, G.K.S. Prakash, A. Molnár, and J. Sommer Superacid Chemistry 2009 John Wiley & Sons, Inc. Hoboken, NJ
10. G.A. Olah, R. Malhotra, S.C. Narang, and J.A. Olah Synthesis 1978 672 673
11. G.A. Olah, P.S. Iyer, and G.K.S. Prakash Synthesis 1986 513 531
12. G.K.S. Prakash, T. Mathew, S. Krishnaraj, E.R. Marinez, and G.A. Olah Appl. Catal., A: Gen. 181 1999 283 288
13. M. Hachoumy, T. Mathew, E.C. Tongco, Y.D. Vankar, G.K.S. Prakash, and G.A. Olah Synlett 1999 363 365
14. G.A. Olah, T. Mathew, M. Farnia, and G.K.S. Prakash Synlett 1999 1067 1068
15. G.A. Olah, T. Mathew, and G.K.S. Prakash Chem. Commun. 2001 1696 1697
16. G.K.S. Prakash, H. Vaghoo, C. Panja, A. Molnár, T. Mathew, and G.A. Olah Synthesis 2008 897 902
17. G.K.S. Prakash, G. Fogassy, and G.A. Olah Catal. Lett. 138 2010 155 159
18. G.K.S. Prakash, K.E. Glinton, C. Panja, L. Gurung, P.T. Battamack, B. Török, T. Mathew, and G.A. Olah Tetrahedron Lett. 53 2012 607 611
19. K. Ishihara, A. Hasegawa, and H. Yamamoto Angew. Chem. Int. Ed. Engl. 40 2001 4077 4079
20. Y. Yin, G. Zhao, and G.L. Li Tetrahedron 61 2005 12042 12052 (and references therein)
21. S. Kobayashi, and S. Nagayama J. Am. Chem. Soc. 120 1998 2985 2986
22. K.P. Boroujeni, and K. Parvanak J. Serb. Chem. Soc. 76 2011 155 163
23. Z. Wang, and B. Gao J. Mol. Catal. A: Chem. 330 2010 35 40
24. T. Okayasu, K. Saito, H. Nishide, and M. Hearn Green Chem. 12 2010 1981 1989
25. G.A. Olah, X.-Y. Li, Q. Wang, and G.K.S. Prakash Synthesis 1993 693 699
26. G.A. Olah, and X.-Y. Li Synlett 1990 267 268
27. G.A. Olah, T. Mathew, A. Goeppert, B. Török, I. Bucsi, X.-Y. Li, Q. Wang, E.R. Marinez, P. Batamack, R. Aniszfeld, and G.K.S. Prakash J. Am. Chem. Soc. 127 2005 5964 5969
28. G.A. Olah, T. Mathew, C. Panja, K. Smith, and G.K.S. Prakash Catal. Lett. 114 2007 1 7
29. G.K.S. Prakash, S. Chacko, C. Panja, T.E. Thomas, L. Gurung, G. Rasul, T. Mathew, and G.A. Olah Adv. Synth. Catal. 351 2009 1567 1574
30. G.K.S. Prakash, S. Chacko, C. Panja, T. Mathew, and G.A. Olah Abstracts of Papers, 230th ACS National Meeting Aug. 28-Sept. 1, 2005, Washington, DC, United States 2005
31. G.K.S. Prakash, A. Shakhmin, K.E. Glinton, S. Rao, T. Mathew, and G.A. Olah Green Chem. 16 2014 3616 3622
32. J. March Advanced Organic Chemistry fourth ed. 1992 Wiley New York, NY
33. G.K.S. Prakash, F. Paknia, S. Chacko, T. Mathew, and G.A. Olah Heterocycles 76 2008 783 799
34. D.A. Klumpp, Y. Zhang, D. Do, and R. Kartika Appl. Catal., A: Gen. 336 2008 128 132
35. D.A. Klumpp, M. Garza, A. Jones, and S. Mendoza J. Org. Chem. 64 1999 6702 6705
36. D.A. Klumpp, P.J. Kindelin, and A. Li Tetrahedron Lett. 46 2005 2931 2935
37. D.A. Klumpp, M. Garza, G.V. Sanchez, S. Lau, and S. Leon J. Org. Chem. 65 2000 8997 9000
38. A.S. Gothelf, T. Hansen, and K.A. Jorgensen J. Chem. Soc., Perkin Trans. 1 2001 854 860
39. M. Abid, and B. Torok Adv. Synth. Catal. 347 2005 1797 1803
40. J. Zhang, P.G. Blazecka, and T.T. Curran Tetrahedron Lett. 48 2007 2611 2615
41. R.K. Singh, S. Jain, N. Sinha, A. Mehta, F. Naqvi, A.K. Agarwal, and N. Anand Tetrahedron Lett. 48 2007 545 548
42. I. Roufos, S.J. Hays, D.J. Dooley, R.D. Schwarz, G.W. Campbell, and A.W. Probert J. Med. Chem. 37 1994 268 274 (and the references therein)
43. I. Roufos, S. Hays, and R.D. Schwarz J. Med. Chem. 39 1996 1514 1520
44. G. Autore, A. Caruso, S. Marzocco, B. Nicolaus, C. Palladino, A. Pinto, A. Popolo, M.S. Sinicropi, G. Tommonaro, and C. Saturnino Molecules 15 2010 2028 2038
45. B.E. Maryanoff, S.O. Nortey, and J.F. Gardocki J. Med. Chem. 27 1984 1067 1071
46. C. De Risi, L. Ferraro, G.P. Pollini, S. Tanganelli, F. Valente, and A.C. Veronese Bioorg. Med. Chem. 16 2008 9904 9910
47. F. Picard, E. Baston, W. Reichert, and R.W. Hartmann Bioorg. Med. Chem. 8 2000 1479 1487
48. F. Picard, S. Barassin, A. Mokhtarian, and R.W. Hartmann J. Med. Chem. 45 2002 3406 3417
49. J. Charton, S. Girault-Mizzi, M.A. Debreu-Fontaine, F. Foufelle, I. Hainault, J.G. Bizot-Espiard, D.H. Caignard, and C. Sergheraert Bioorg. Med. Chem. 14 2006 4490 4518
50. R.S. Dothager, K.S. Putt, B.J. Allen, B.J. Leslie, V. Nesterenko, and P.J. Hergenrother J. Am. Chem. Soc. 127 2005 8686 8696
51. M. Graffner-Nordberg, K. Kolmodin, J. Aqvist, S.F. Queener, and A. Hallberg Eur. J. Pharm. Sci. 22 2004 43 54
52. C. Kaiser, C.J. Spagnuolo, T.C. Adams, V.H. Audia, A.C. Dupont, H. Hatoum, V.C. Lowe, J.C. Prosser, B.L. Sturm, and L. Noronha-Blob J. Med. Chem. 35 1992 4415 4424
53. P. Strazzolini, A.G. Giumanini, and G. Verardo Synth. Commun. 17 1987 1919 1928 (and references therein)
54. Y. Takahashi, N. Yoneda, and H. Nagai Chem. Lett. 1985 1733 1734
55. M.J. Earle, R.A. Fairhurst, and H. Heaney Tetrahedron Lett. 32 1991 6171 6174
56. K. Takahashi, K. Shibasaki, K. Ogura, and H. Iida J. Org. Chem. 48 1983 3566 3569
57. J. Tang, R. Zhang, and J. Shen Synth. Met. 155 2005 100 104
58. R.R. Naredla, and D.A. Klumpp Chem. Rev. 113 2013 6905 6948
59. G.A. Olah, and D.A. Klumpp Superelectrophiles and Their Chemistry 2008 Wiley-Interscience Hoboken, NJ
60. G.A. Olah, and D.A. Klumpp Acc. Chem. Res. 37 2004 211 220
61. G.A. Olah, and M. Calin J. Am. Chem. Soc. 90 1968 4672 4675
62. T. Yamazaki, S.-i. Saito, T. Ohwada, and K. Shudo Tetrahedron Lett. 36 1995 5749 5752
63. D.A. Klumpp, S. Lau, M. Garza, B. Schick, and K. Kantardjieff J. Org. Chem. 64 1999 7635 7637
64. J. Perez-Prieto, R.E. Galian, and M.C. Morant-Minana ChemPhysChem 7 2006 2077 2080
65. T.B. Adams, M.M. McGowen, M.C. Williams, S.M. Cohen, V.J. Feron, J.I. Goodman, L.J. Marnett, I.C. Munro, P.S. Portoghese, R.L. Smith, and W.J. Waddell Food Chem. Toxicol. 45 2007 171 180
66. M. Cabrera, M. Simoens, G. Falchi, M.L. Lavaggi, O.E. Piro, E.E. Castellano, A. Vidal, A. Azqueta, A. Monge, A.L. Cerain, G. Sagrera, G. Seoane, H. Cerecettoa, and M. Gonzaleza Bioorg. Med. Chem. 15 2007 3356 3367
67. K. Nakamura, R. Yamanaka, T. Matsuda, and T. Harada Tetrahedron: Asymmetry 14 2003 2659 2681
68. E.B. Kurbanoglu, K. Zilbeyaz, N.I. Kurbanogluc, and M. Taskin Tetrahedron: Asymmetry 18 2007 1529 1532
69. M.L. Patil, H.B. Borate, D.E. Ponde, and V.H. Deshpande Tetrahedron 58 2002 6615 6620
70. V. Premasagar, V.A. Palaniswamy, and E.J. Eisenbraun J. Org. Chem. 46 1981 2974 2976
71. Y. Sato, M. Yato, T. Ohwada, S. Saito, and K. Shudo J. Am. Chem. Soc. 117 1995 3037 3043
72. F. Effenberger, and G. Epple Angew. Chem. Int. Ed. 11 1972 299 300
73. F. Effenberger, and G. Epple Angew. Chem. Int. Ed. 11 1972 300 301
74. T. Yamato, C. Hideshima, G.K.S. Prakash, and G.A. Olah J. Org. Chem. 56 1991 3955 3957
75. G.K.S. Prakash, P. Yan, B. Török, I. Bucsi, M. Tanaka, and G.A. Olah Catal. Lett. 85 2003 1 6
76. Y. Matsushita, K. Sugamoto, and T. Matsui Tetrahedron Lett. 45 2004 4723 4727
77. B. Chiche, A. Finiels, C. Gauthier, P. Geneste, J. Graille, and D. Pioch J. Org. Chem. 51 1986 2128 2130
78. K. Shimizu, K. Niimi, and A. Satsuma Catal. Commun. 9 2008 980 983
79. M.H. Sarvari, and H. Sharghi J. Org. Chem. 69 2004 6953 6956
80. G. Sartori, and R. Maggi Chem. Rev. 106 2006 1077 1104
81. G.P. Schiemenz, and U. Schmidt Liebigs Ann. Chem. 1976 1514 1519
82. G.A. Olah, R. Malhotra, S.C. Narang, and J.A. Olah Synthesis 1978 672 673
83. G.A. Olah, E. Zadok, R. Edler, D.H. Adamson, W. Kasha, and G.K.S. Prakash J. Am. Chem. Soc. 111 1989 9123 9125
84. G.A. Olah, A. Germain, H.C. Lin, and D. Forsyth J. Am. Chem. Soc. 97 1975 2928 2929
85. G.A. Olah Angew. Chem. Int. Ed. 32 1993 767 788
86. T. Ohwada, N. Yamagata, and K. Shudo J. Am. Chem. Soc. 113 1991 1364 1373
87. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven, K.N. Kudin, and J.C. Burant Gaussian 09, Revision A.02 2009 Gaussian, Inc. Wallingford, CT
88. J.B. Foresman, and A. Frisch Exploring Chemistry with Electronic Structure Methods 1996 Gaussian Inc. Pittsburgh 1 64
89. J.E. Miline, T. Storz, J.T. Colyer, O.R. Thiel, M.D. Seran, R.D. Larsen, and J.A. Murry J. Org. Chem. 76 2011 9519 9524
90. C. Schnabel, K. Sterz, H. Mueller, J. Rehbein, M. Wiese, and M. Hiersemann J. Org. Chem. 76 2011 512 522
91. J.R. Coats, J.W. Williams, C. Chang, A.H. Lee, and R.L. Metcalf Environ. Toxicol. Chem. 8 1989 45 52
92. Y. Iwakura, F. Toda, M. Kosugi, and Y. Torii J. Org. Chem. 36 1970 3990 3992
93. R.C. Fuson, and M.L. Ward J. Am. Chem. Soc. 68 1946 521 522
94. G. Werber, and F. Buccheri Gaz. Chim. Ital. 96 1966 465 474
95. Y. Takahashi, N. Yoneda, and H. Nagai Chem. Lett. 11 1985 1733 1734