Perchloric acid catalyzed homogeneous and heterogeneous addition of β-dicarbonyl compounds to alcohols and alkenes and investigation of the mechanism

Journal of Organic Chemistry

Volumn 75, Issue 15, 2010, Pages 5017-5030

  Liu, Pei Nian ^a,b   Dang, Li ^c   Wang, Qing Wei ^a   Zhao, Shu Lei ^a   Xia, Fei ^a   Ren, Yu Jie ^a   Gong, Xue Qing ^a   Chen, Jun Qin ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b LANZHOU UNIVERSITY   (China)

^c HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; KETONES; OLEFINS; SILICA; SILICA GEL;

CATALYTIC ABILITY; CATALYZED REACTIONS; DFT CALCULATION; DICARBONYL COMPOUNDS; DIKETONES; HIGHER YIELD; PERCHLORIC ACIDS; SECONDARY ALCOHOLS; SUPPORTED CATALYSTS;

INORGANIC ACIDS;

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; BRONSTED ACID; CARBONYL DERIVATIVE; PERCHLORIC ACID; SILICA GEL;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY;

EID: 84962406536     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100517k     Document Type: Article

References (104)

1. March, J. Advanced Organic Chemistry, 4 th ed.; Wiley: New York, 1992.
2. Current Trends in Organic Synthesis; Scolastico, C. and Nicotra, F., Eds.; Plenum: New York, 1999.
3. Anastas, P. T. and Warner, J. C. Green Chemistry: Theory and Practice; Oxford University, Press: New York, 1988.
4. Matlack, A. S. Introduction to Green Chemistry; Marcel Dekker Inc.: New York, 2001.
5. Lancester, M. Green Chemistry: An Introductory Text; Royal Society of Chemistry: Cambridge, 2002.
6. Clark, J. H. and Macquarrie, D. Handbook of Green Chemistry & Technology; Blackwell Publishers: Oxford, 2002.
7. Guillena, G.; Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2007, 46, 2358
8. Yasuda, M.; Somyo, T.; Baba, A. Angew. Chem., Int. Ed. 2006, 45, 793
9. Vicennati, P.; Cozzi, P. G. Eur. J. Org. Chem. 2007, 2248
10. Kischel, J.; Mertins, K.; Michalik, D.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2007, 349, 865
11. Yuan, Y.; Shi, Z.; Feng, X.; Liu, X. Appl. Organomet. Chem. 2007, 21, 958
12. Jana, U.; Biswas, S.; Maiti, S. Tetrahedron Lett. 2007, 48, 4065
13. Rueping, M.; Nachtsheim, B. J.; Kuenkel, A. Org. Lett. 2007, 9, 825
14. Noji, M.; Konno, Y.; Ishii, K. J. Org. Chem. 2007, 72, 5161
15. Huang, W.; Wang, J.; Shen, Q.; Zhou, X. Tetrahedron Lett. 2007, 48, 3969
16. Motokura, K.; Fujita, N.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Angew. Chem., Int. Ed. 2006, 45, 2605
17. Motokura, K.; Nakagiri, N.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Org. Chem. 2007, 72, 6006
18. Shirakawa, S.; Kobayashi, S. Org. Lett. 2007, 9, 311
19. Sanz, R.; Martínez, A.; Miguel, D.; Álvarez- Gutiérrez, J. M.; Rodríguez, F. Adv. Synth. Catal. 2006, 348, 1841
20. Sanz, R.; Miguel, D.; Martínez, A.; Álvarez- Gutiérrez, J. M.; Rodríguez, F. Org. Lett. 2007, 9, 727
21. Sanz, R.; Miguel, D.; Martínez, A.; Álvarez- Gutiérrez, J. M.; Rodríguez, F. Org. Lett. 2007, 9, 2027
22. Wang, G.-W.; Shen, Y. -B.; Wu, X.-L. Eur. J. Org. Chem. 2008, 29, 4999
23. Liu, P. N.; Zhou, Z. Y.; Lau, C. P. Chem.- Eur. J. 2007, 13, 8610
24. See Supporting Information.
25. Trost, B. M. Science 1991, 254, 1471
26. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259
27. Trost, B. M. Acc. Chem. Res. 2002, 35, 695
28. Pei, T.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11290
29. Pei, T.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 648
30. Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 2056
31. Han, X.; Wang, X.; Pei, T.; Widenhoefer, R. A. Chem.- Eur. J. 2004, 10, 6333
32. Leitner, A.; Larsen, J.; Steffens, C.; Hartwig, J. F. J. Org. Chem. 2004, 69, 7552
33. Wang, X.; Widenhoefer, R. A. Chem. Commun. 2004, 660
34. Yao, X.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884
35. Nguyen, R.-V.; Yao, X.-Q.; Bohle, D. S.; Li, C.-J. Org. Lett. 2005, 7, 673
36. Yao, X.; Li, C.-J. J. Org. Chem. 2005, 70, 5752
37. Rueping, M.; Nachtsheim, B.; J. Kuenkel, A. Synlett 2007, 9, 1391
38. Duan, Z.; Xuan, X.; Wu, Y. Tetrahedron Lett. 2007, 48, 5157
39. Li, Y.; Yu, Z.; Wu, S. J. Org. Chem. 2008, 73, 5647
40. Wang, G.-W.; Shen, Y.-B.; Wu, X.-L.; Wang, L. Tetrahedron Lett. 2008, 49, 5090
41. Melero, J. A.; Iglesias, J.; Morales, G. Green Chem. 2009, 11, 1285
42. Gu, Y.; Li, G. Adv. Synth. Catal. 2009, 351, 817
43. Song, C. E.; Lee, S. Chem. Rev. 2002, 102, 3495
44. Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385
45. Vos, D. E. D.; Dams, M.; Sels, B. F; Jacobs, P. A. Chem. Rev. 2002, 102, 3615
46. Liu, P. N.; Xia, F.; Wang, Q. W.; Ren, Y. J.; Chen, J. Q. Green. Chem. 2010, 12, 1049
47. 2 as the catalyst: Shaterian, H. R.; Yarahmadi, H.; Ghashang, M. Tetrahedron 2008, 64, 1263
48. Chakraborti, A. K.; Gulhane, R. Chem. Commun. 2003, 1896
49. Kumar, R.; Kumar, D.; Chakraborti, A. K. Synthesis 2007, 299
50. Shaterian, H.; Shahrekipoor, R.; Ghashang, F. M. J. Mol. Catal. A: Chem. 2007, 272, 142
51. Das, B.; Laxminarayana, K.; Ravikanth, B. J. Mol. Catal. A: Chem. 2007, 271, 131
52. Kantevari, S.; Bantu, R.; Nagarapu, L. J. Mol. Catal. A: Chem. 2007, 269, 53
53. Bigdeli, M. A.; Heravi, M. M.; Mahdavinia, G. H. J. Mol. Catal. A: Chem. 2007, 275, 25
54. Das, B.; Damodar, K.; Chowdhury, N.; Kumar, R. A. J. Mol. Catal. A: Chem. 2007, 274, 148
55. Kamble, V. T.; Jamode, V. S.; Joshi, N. S.; Biradara, A. V.; Deshmukh, R. Y. Tetrahedron Lett. 2006, 47, 5573
56. Das, B.; Venkateswarlu, K.; Majhi, A.; Reddy, M. R.; Reddy, K. N.; Rao, Y. K.; Ravikumar, K.; Sridhar, B. J. Mol. Catal. A: Chem. 2006, 246, 276
57. Das, B.; Venkateswarlu, K.; Suneel, K.; Majhi, A. Tetrahedron Lett. 2007, 48, 5371
58. Khatik, G. L.; Sharma, G.; Kumar, R.; Chakraborti, A. K. Tetrahedron 2007, 63, 1200
59. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 4689
60. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 4691
61. Richard, J. P.; Rothenberg, M. E.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1361
62. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1373
63. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1383
64. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1396
65. Ta-Shama, R.; Jencks, W. P. J. Am. Chem. Soc. 1986, 108, 8040
66. Li, X.; Ye, S.; He, C.; Yu, Z.-X. Eur. J. Org. Chem. 2008, 4296
67. Akiyama, T. Chem. Rev. 2007, 107, 5744
68. Terada, M. Chem. Commun. 2008, 4097
69. Doyle, A. D.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713
70. Xu, S.; Wang, Z.; Zhang, X.; Ding, K. Angew. Chem., Int. Ed. 2008, 47, 2840
71. Akiyama, T.; Itoh, J.; Yokota, D.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566
72. Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356
73. Terada, M.; Tanaka, H.; Sorimachi, K. J. Am. Chem. Soc. 2009, 131, 3430
74. Lu, M.; Zhu, D.; Lu, Y.; Zeng, X.; Tan, B.; Xu, Z.; Zhong, G. J. Am. Chem. Soc. 2009, 131, 4562
75. Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012
76. Zhang, X.; Du, H.; Wang, Z.; Wu, Y.-D.; Ding, K. J. Org. Chem. 2006, 71, 2862
77. Gridnev, I. D.; Kouchi, M.; Sorimachi, K.; Terada, M. Tetrahedron Lett. 2007, 48, 497
78. Yamanaka, M.; Itoh, J.; Fuchibe, K.; Akiyama, T. J. Am. Chem. Soc. 2007, 129, 6756
79. Simón, L.; Goodman, J. M. J. Am. Chem. Soc. 2008, 130, 8741
80. Anderson, C. D.; Dudding, T.; Gordillo, R.; Houk, K. N. Org. Lett. 2008, 10, 2749
81. Diaz, D. D.; Martín, V. S. Tetrahedron Lett. 2000, 41, 9993
82. Schlund, S.; Janke, E. M. B.; Weisz, K.; Engels, B. J. Comput. Chem. 2010, 31, 665
83. Drexler, E. J.; Field, K. W. J. Chem. Educ. 1976, 53, 392
84. Chan, S. I.; Lin, L.; Clutter, D.; Dea, P. Proc. Natl. Acad. Sci. U.S.A. 1970, 65, 316
85. Noji, M.; Ohno, T.; Fuji, K.; Futaba, N.; Tajima, H.; Ishii, K. J. Org. Chem. 2003, 68, 9340
86. Alesso, E.; Torviso, R.; Erlich, M.; Finkielsztein, L.; Lantaño, B.; Moltrasio, G.; Aguirre, J.; Vázquez, P.; Pizzio, L.; Cáceres, C.; Blanco, M.; Thomas, H. Synth. Commun. 2002, 3803
87. Xu, T.; Haw, J. F. J. Am. Chem. Soc. 1994, 116, 10188
88. Mayo, F. R. J. Am. Chem. Soc. 1968, 90, 1289
89. Li, Z. P.; Cao, L.; Li, C. J. Angew. Chem., Int. Ed. 2007, 46, 6505
90. Yadav, J. S.; Subba, B. V. R.; Pandurangam, T.; Raghavendra, K. V. R.; Praneeth, K.; Narayana, G. G. K. S. K.; Madavi, C.; Kunwar, A. C. Tetrahedron Lett. 2008, 49, 4296
91. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
92. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200
93. Lee, C.; Yang, W.; Parr, G. Phys. Rev. B 1988, 37, 785
94. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F. J. Phys. Chem. 1994, 98, 11623
95. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299
96. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111
97. Höllwarth, A.; Böhme, M.; Dapprich, S.; Ehlers, A. W.; Obbi, A. G.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237
98. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
99. Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163
100. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta. 1973, 28, 213
101. Binning, R. C., Jr.; Curtiss, L. A. J. Comput. Chem. 1990, 11, 1206
102. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999
103. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117
104. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.