Computation-guided development of Au-catalyzed cycloisomerizations proceeding via 1,2-Si or 1,2-H migrations: Regiodivergent synthesis of silylfurans

Journal of the American Chemical Society

Volumn 132, Issue 22, 2010, Pages 7645-7655

  Dudnik, Alexander S ^a   Xia, Yuanzhi ^b,c   Li, Yahong ^b,c   Gevorgyan, Vladimir ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b SOOCHOW UNIVERSITY   (China)

^c QINGHAI INSTITUTE OF SALT LAKES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENYL; ARYL GROUP; AU SPECIES; CARBENES; CATALYTIC TRANSFORMATION; CHARGED INTERMEDIATES; COMPUTATIONAL RESULTS; COUNTERIONS; CYCLOISOMERIZATIONS; DFT CALCULATION; EXPERIMENTAL DATA; H MIGRATION; MIGRATION PRODUCTS; NON-POLAR SOLVENTS; POLAR MEDIA; POLAR SOLVENTS; PROPARGYL; RATIONAL DESIGN; SOLVENT EFFECTS; TRIFLATES;

HYDROCARBONS; KETONES; REACTION INTERMEDIATES; SILICON; SOLVENTS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

CYCLIZATION;

CARBENE; COUNTERION; FURAN DERIVATIVE; GOLD; KETONE DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DENSITY FUNCTIONAL THEORY; ISOMERIZATION; KINETICS; POLARIZATION; PROTON TRANSPORT; SIMULATION; SYNTHESIS;

CATALYSIS; CYCLIZATION; FURANS; GOLD; ISOMERISM; KETONES; MODELS, CHEMICAL; QUANTUM THEORY; SILANES;

EID: 77953116518     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja910290c     Document Type: Article

References (119)

1. For selected reviews on transition-metal-catalyzed transformations of alkynes and allenes, see
2. Alonso, F., Beletskaya, I. P., and Yus, M. Chem. Rev. 2004, 104, 3079
3. Kirsch, S. F. Synthesis 2008, 3183
4. Nakamura, I. and Yamamoto, Y. Chem. Rev. 2004, 104, 2127
5. Patil, N. T. and Yamamoto, Y. Chem. Rev. 2008, 108, 3395
6. Jiménez-Núñez, E. and Echavarren, A. M. Chem. Commun. 2007, 333
7. Crone, B. and Kirsch, S. F. Chem.-Eur. J. 2008, 14, 3514
8. Rubin, M., Sromek, A. W., and Gevorgyan, V. Synlett 2003, 2265
9. Ma, S. Chem. Rev. 2005, 105, 2829
10. Bates, R. W. and Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12
11. Zimmer, R., Dinesh, C. U., Nandanan, E., and Khan, F. A. Chem. Rev. 2000, 100, 3067
12. Abu Sohel, S. M. and Liu, R.-S. Chem. Soc. Rev. 2009, 38, 2269
13. Majumdar, K. C., Debnath, P., and Roy, B. Heterocycles 2009, 78, 2661
14. Hashmi, A. S. K., Schwarz, L., Choi, J.-H., and Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285
15. Zhou, C. Y., Chan, P. W. H., and Che, C. M. Org. Lett. 2006, 8, 325
16. For selected recent reviews on Au-chemistry, see
17. Arcadi, A. Chem. Rev. 2008, 108, 3266
18. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180
19. Gorin, D. J. and Toste, F. D. Nature 2007, 446, 395
20. Li, Z., Brouwer, C., and He, C. Chem. Rev. 2008, 108, 3239
21. Fürstner, A. and Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410
22. Jiménez-Núñez, E. and Echavarren, A. M. Chem. Rev. 2008, 109, 3326
23. Widenhoefer, R. A. and Han, X. Eur. J. Org. Chem. 2006, 4555
24. Shen, H. C. Tetrahedron 2008, 64, 3885
25. Shen, H. C. Tetrahedron 2008, 64, 7847
26. Hashmi, A. S. K. and Hutchings, G. J. Angew. Chem., Int. Ed. 2006, 45, 7896
27. Belmont, P. and Parker, E. Eur. J. Org. Chem. 2009, 6075
28. Hoffmann-Röder, A. and Krause, N. Org. Biomol. Chem. 2005, 3, 387
29. For recent reviews on furan synthesis, see
30. Brown, R. C. D. Angew. Chem., Int. Ed. 2005, 44, 850
31. Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076
32. Patil, N. T. and Yamamoto, Y. ARKIVOC 2007, 121
33. Hou, X. L., Cheung, H. Y., Hon, T. Y., Kwan, P. L., Lo, T. H., Tong, S. Y., and Wong, H. N. C. Tetrahedron 1998, 54, 1955
34. Hou, X.-L., Yang, Z., Yeung, K.-S., and Wong, H. N. C. Prog. Heterocycl. Chem. 2008, 19, 176
35. Balme, G., Bouyssi, D., and Monteiro, N. Heterocycles 2007, 73, 87
36. DSouza, D. M. and Muller, T. J. J. Chem. Soc. Rev. 2007, 36, 1095 For selected recent examples on transition-metal-catalyzed synthesis of furans, see:
37. Zhang, M., Jiang, H.-F., Neumann, H., Beller, M., and Dixneuf, P. H. Angew. Chem., Int. Ed. 2009, 48, 1681
38. Xiao, Y. and Zhang, J. Adv. Synth. Catal. 2009, 351, 617
39. Pan, Y.-M., Zhao, S.-Y., Ji, W.-H., and Zhan, Z.-P. J. Comb. Chem. 2009, 11, 103
40. Zhang, G., Huang, X., Li, G., and Zhang, L. J. Am. Chem. Soc. 2008, 130, 1814
41. Xiao, Y. and Zhang, J. Angew. Chem., Int. Ed. 2008, 47, 1903
42. Shibata, Y., Noguchi, K., Hirano, M., and Tanaka, K. Org. Lett. 2008, 10, 2825
43. Ji, K.-G., Shen, Y.-W., Shu, X.-Z., Xiao, H.-Q., Bian, Y.-J., and Liang, Y.-M. Adv. Synth. Catal. 2008, 350, 1275
44. Barluenga, J., Riesgo, L., Vicente, R., López, L. A., and Tomás, M. J. Am. Chem. Soc. 2008, 130, 13528
45. Aurrecoechea, J. M., Durana, A., and Pérez, E. J. Org. Chem. 2008, 73, 3650
46. Zhao, L.-B., Guan, Z.-H., Han, Y., Xie, Y.-X., He, S., and Liang, Y.-M. J. Org. Chem. 2007, 72, 10276
47. Shu, X.-Z., Liu, X.-Y., Xiao, H.-Q., Ji, K.-G., Guo, L.-N., Qi, C.-Z., and Liang, Y.-M. Adv. Synth. Catal. 2007, 349, 2493
48. Peng, L., Zhang, X., Ma, M., and Wang, J. Angew. Chem., Int. Ed. 2007, 46, 1905
49. Arimitsu, S. and Hammond, G. B. J. Org. Chem. 2007, 72, 8559
50. Zhang, J. and Schmalz, H.-G. Angew. Chem., Int. Ed. 2006, 45, 6704
51. Aponick, A., Li, C.-Y., Malinge, J., and Marques, E. F. Org. Lett. 2009, 11, 4624
52. Blanc, A., Tenbrink, K., Weibel, J.-M., and Pale, P. J. Org. Chem. 2009, 74, 5342
53. Blanc, A., Tenbrink, K., Weibel, J.-M., and Pale, P. J. Org. Chem. 2009, 74, 4360
54. Yoshida, M., Al-Amin, M., and Shishido, K. Synthesis 2009, 2454
55. Egi, M., Azechi, K., and Akai, S. Org 2009, 11, 5002
56. Liu, F., Yu, Y., and Zhang, J. Angew Chem., Int. Ed. 2009, 48, 5505
57. Suhre, M. H., Reif, M., and Kirsch, S. F. Org. Lett. 2005, 7, 3925
58. Patil, N. T., Wu, H., and Yamamoto, Y. J. Org. Chem. 2005, 70, 4531
59. Liu, Y., Song, F., Song, Z., Liu, M., and Yan, B. Org. Lett. 2005, 7, 5409
60. Yao, T., Zhang, X., and Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164
61. Hashmi, A. S. K. and Sinha, P. Adv Synth. Catal. 2004, 346, 432
62. Kelin, A. V. and Gevorgyan, V. J. Org. Chem. 2002, 67, 95
63. For Ag-catalyzed synthesis of furans via a formal 1,2-H shift in allenones, see
64. Marshall, J. A. and Robinson, E. D. J. Org. Chem. 1990, 55, 3450
65. Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1995, 34, 1581
66. For selected examples on 1,2-shifts in the synthesis of aromatic heterocycles, see
67. Kim, J. T., Kelin, A. V., and Gevorgyan, V. Angew. Chem., Int. Ed. 2003, 42, 98
68. Sromek, A. W., Kelin, A. V., and Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280
69. Schwier, T., Sromek, A. W., Yap, D. M. L., Chernyak, D., and Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 9868
70. Dudnik, A. S. and Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 5195
71. Dudnik, A. S., Sromek, A. W., Rubina, M., Kim, J. T., Kelin, A. V., and Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 1440
72. Gorin, D. J., Davis, N. R., and Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260
73. Li, G., Huang, X., and Zhang, L. Angew. Chem., Int. Ed. 2008, 47, 346
74. Takaya, J., Udagawa, S., Kusama, H., and Iwasawa, N. Angew. Chem., Int. Ed. 2008, 47, 4906
75. Davies, P. W. and Martin, N. Org. Lett. 2009, 11, 2293
76. Sromek, A. W., Rubina, M., and Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 10500
77. Xia, Y., Dudnik, A. S., Gevorgyan, V., and Li, Y. J. Am. Chem. Soc. 2008, 130, 6940
78. For selected examples, see
79. Danheiser, R. L., Carini, D. J., and Basak, A. J. Am. Chem. Soc. 1981, 103, 1604
80. Danheiser, R. L., Kwasigroch, C. A., and Tsai, Y.-M. J. Am. Chem. Soc. 1985, 107, 7233
81. Becker, D. A. and Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389
82. Panek, J. S. and Yang, M. J. Am. Chem. Soc. 1991, 113, 9868
83. For selected examples of Si-shifts in the synthesis of aromatic heterocycles, see
84. Nakamura, I., Sato, T., Terada, M., and Yamamoto, Y. Org. Lett. 2007, 9, 4081
85. Seregin, I. V. and Gevorgyan, V. J. Am. Chem. Soc. 2006, 128, 12050
86. Danheiser, R. L., Stoner, E. J., Koyama, H., Yamashita, D. S., and Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407
87. Creary, X. and Butchko, M. A. J. Org. Chem. 2001, 66, 1115
88. Creary, X. and Wang, Y.-X. Tetrahedron Lett. 1989, 30, 2493
89. Creary, X. and Butchko, M. A. J. Org. Chem. 2002, 67, 112
90. For selected examples of DFT studies in Au-chemistry, see
91. Nevado, C. and Echavarren, A. M. Chem.-Eur. J. 2005, 11, 3155
92. Comas-Vives, A., González-Arellano, C., Corma, A., Iglisias, M., Sánchez, F., and Ujaque, G. J. Am. Chem. Soc. 2006, 128, 4756
93. Nieto-Oberhuber, C., López, S., Muñoz, M. P., Cárdenas, D. J., Buñuel, E., Nevado, C., and Echavarren, A. M. Angew. Chem., Int. Ed. 2005, 44, 6146
94. Faza, O. N., López, C. S., Álvarez, R., and de Lera, A. R. J. Am. Chem. Soc. 2006, 128, 2434
95. Straub, B. F. Chem. Commun. 2004, 1726
96. Correa, A., Marion, N., Fensterbank, L., Malacria, M., Nolan, S. P., and Cavallo, L. Angew. Chem., Int. Ed. 2008, 47, 718
97. Nieto-Oberhuber, C., Muñoz, M. P., Buñuel, E., Nevado, C., Cárdenas, D. J., and Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402
98. Shi, F.-Q., Li, X., Xia, Y., Zhang, L., and Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 15503
99. Lemière, G., Gandon, V., Cariou, K., Hours, A., Fukuyama, T., Dhimane, A.-L., Fensterbank, L., and Malacria, M. J. Am. Chem. Soc. 2009, 131, 2993
100. Nieto-Oberhuber, C., Pérez-Galán, P., Herrero-Gómez, E., Lauterbach, T., Rodríguez, C., López, S., Bour, C., Rosellón, A., Cárdenas, D. J., and Echavarren, A. M. J. Am. Chem. Soc. 2008, 130, 269
101. B3LYP/6-31G (LANL2DZ for Au) method was used for all the calculations, and solvation effect was calculated by CPCM model.
102. See Supporting Information for details.
103. Sheng, H., Lin, S., and Huang, Y. Synthesis 1987, 1022
104. Fukuda, Y., Shiragami, H., Utimoto, K., and Nozaki, H. J. Org. Chem. 1991, 56, 5816
105. Shapiro, N. D. and Toste, F. D. J. Am. Chem. Soc. 2007, 129, 4160
106. Wang, W., Xu, B., and Hammond, G. B. J. Org. Chem. 2009, 74, 1640
107. For examples of the proposed β-electrophilic attack on vinyl-gold, see
108. Huang, X. and Zhang, L. J. Am. Chem. Soc. 2007, 129, 6398
109. Luzung, M. R., Mauleón, P., and Toste, F. D. J. Am. Chem. Soc. 2007, 129, 12402
110. For review on counterion effects in Au-catalysis, see
111. Gorin, D. J., Sherry, B. D., and Toste, F. D. Chem. Rev. 2008, 108, 3351 For selected examples, see
112. Lemière, G., Gandon, V., Agenet, N., Goddard, J.-P., de Kozak, A., Aubert, C., Fensterbank, L., and Malacria, M. Angew. Chem., Int. Ed. 2006, 45, 7596
113. Bhunia, S. and Liu, R.-S. J. Am. Chem. Soc. 2008, 130, 16488
114. Gorin, D. G., Watson, I. D. G., and Toste, F. D. J. Am. Chem. Soc. 2008, 130, 3736
115. Kovács, G., Ujaque, G., and Lledós, A. J. Am. Chem. Soc. 2008, 130, 853
116. --counterion base. See Supporting Information for details.
117. For a single example of a solvent effect in the Au-catalyzed synthesis of pyrroles, see ref 7i.
118. For review on silylfurans, see
119. Keay, B. A. Chem. Soc. Rev. 1999, 28, 209