Cyclization of aromatic propargyl alcohol with a thiophene group yielding naphthothiophene aldehyde induced by a ruthenium complex

Chemistry - A European Journal

Volumn 18, Issue 11, 2012, Pages 3399-3407

  Tsai, Fu Yuan ^a   Ma, Hao Wei ^a   Huang, Shou Ling ^a   Lin, Ying Chih ^a   Wang, Yu ^a   Liu, Yi Hung ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

aldehydes; cyclization; fused ring systems; oxidation; ruthenium

Indexed keywords

ALLENYLIDENE COMPLEXES; CARBENE COMPLEXES; CARBENE LIGANDS; CYCLOPENTADIENYLS; FERROCENES; FUSED-RING SYSTEM; HIGH YIELD; LOW TEMPERATURES; METAL CENTERS; PHOSPHANE LIGANDS; PROPARGYL ALCOHOL; PROPARGYLIC ALCOHOLS; ROOM TEMPERATURE; RUTHENIUM COMPLEXES; SIDE PRODUCTS; SOLVENT SYSTEM; THIOPHENE GROUP; TRIPLE BONDS;

ALCOHOLS; ALDEHYDES; ESTERIFICATION; ESTERS; IRON COMPOUNDS; LIGANDS; ORGANOMETALLICS; OXIDATION; OXYGENATION; OXYGENATORS; RUTHENIUM; RUTHENIUM COMPOUNDS; THIOPHENE; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

CYCLIZATION;

EID: 84863238068     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103161     Document Type: Article

References (122)

1. M. I. Bruce, Chem. Rev. 1998, 98, 2797-2858
2. D. Touchard, P. H. Dixneuf, Coord. Chem. Rev. 1998, 178-180, 409-429
3. V. Cadierno, M. P. Gamasa, J. Gimeno, Eur. J. Inorg. Chem. 2001, 571-591
4. R. F. Winter, S. Zalis, Coord. Chem. Rev. 2004, 248, 1565-1583
5. S. Rigaut, D. Touchard, P. H. Dixneuf, Coord. Chem. Rev. 2004, 248, 1585-1601
6. V. Cadierno, M. P. Gamasa, J. Gimeno, Coord. Chem. Rev. 2004, 248, 1627-1657.
7. C. Bruneau, P. H. Dixneuf, Angew. Chem. 2006, 118, 2232-2260
8. Angew. Chem. Int. Ed. 2006, 45, 2176-2203
9. V. Cadierno, J. Gimeno, Chem. Rev. 2009, 109, 3512-3560
10. B. M. Trost, A. McClory, Chem. Asian J. 2008, 3, 164-194.
11. H. Matsuzawa, Y. Miyake, Y. Nishibayashi, Angew. Chem. 2007, 119, 6608-6611
12. Angew. Chem. Int. Ed. 2007, 46, 6488-6491
13. H. Matsuzawa, K. Kanao, Y. Miyake, Y. Nishibayashi, Org. Lett. 2007, 9, 5561-5564
14. K. Kanao, H. Matsuzawa, Y. Miyake, Y. Nishibayashi, Synthesis 2008, 23, 3869-3873
15. K. Kanao, Y. Miyake, Y. Nishibayashi, Organometallics 2009, 28, 2920-2926
16. M. Ikeda, Y. Miyake, Y. Nishibayashi, Angew. Chem. 2010, 122, 7447-7451
17. Angew. Chem. Int. Ed. 2010, 49, 7289-7293.
18. J. P. Selegue, Coord. Chem. Rev. 2004, 248, 1543-1563.
19. J. Barluenga, J. Santamaría, M. Tomás, Chem. Rev. 2004, 104, 2259-2283
20. C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813-834
21. N. Chatani, T. Morimoto, T. Muto, S. Murai, J. Am. Chem. Soc. 1994, 116, 6049-6050.
22. A. Fürstner, H. Szillat, F. Stelzer, J. Am. Chem. Soc. 2000, 122, 6785-6786
23. E. Soriano, P. Ballesteros, J. Marco-Contelles, Organometallics 2005, 24, 3182-3191
24. C. Fehr, J. Galindo, Angew. Chem. 2006, 118, 2967-2970
25. Angew. Chem. Int. Ed. 2006, 45, 2901-2904
26. A. Fürstner, L. Morency, Angew. Chem. 2008, 120, 5108-5111
27. Angew. Chem. Int. Ed. 2008, 47, 5030-5033
28. B. D. Sherry, L. Maus, B. N. Laforteza, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 8132-8133
29. E. s. Jime'nez-Nu'nez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350
30. C. Nieto-Oberhuber, S. López, M. P. Muñoz, D. J. Cárdenas, E. Buñuel, C. Nevado, A. M. Echavarren, Angew. Chem. 2005, 117, 6302-6304
31. Angew. Chem. Int. Ed. 2005, 44, 6146-6148
32. S. Ma, S. Yu, Z. Gu, Angew. Chem. 2006, 118, 206-209
33. Angew. Chem. Int. Ed. 2006, 45, 200-203.
34. B. M. Novak, R. H. Grubbs, J. Am. Chem. Soc. 1988, 110, 960-961
35. M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953-956
36. R. H. Grubbs, W. Tumas, Science 1989, 243, 907-915.
37. K. H. Dötz, Angew. Chem. 1975, 87, 672-673
38. Angew. Chem. Int. Ed. Engl. 1975, 14, 644-645
39. K. H. Dötz, R. Dietz, A. von Imhof, H. Lorenz, G. Huttner, Chem. Ber. 1976, 109, 2033-2038
40. M. L. Waters, W. D. Wulff, Org. React. 2008, 70, 121-623
41. M. Rawat, W. D. Wulff, Org. Lett. 2004, 6, 329-332
42. J. D. White, H. Smits, Org. Lett. 2005, 7, 235-238.
43. J. Barluenga, F. Aznar, S. Barluenga, M. Fernández, A. Martín, S. García-Granda, A. Piñera-Nicolás, Chem. Eur. J. 1998, 4, 2280-2298
44. J. Barluenga, R. M. Canteli, J. Flórez, S. García-Granda, A. Gutiérrez-Rodríguez, J. Am. Chem. Soc. 1994, 116, 6949-6950
45. C. A. Merlic, D. Xu, J. Am. Chem. Soc. 1991, 113, 7418-7420
46. K. H. Dötz, W. Kuhn, G. Müller, B. Huber, H. G. Alt, Angew. Chem. 1986, 98, 826-827
47. Angew. Chem. Int. Ed. Engl. 1986, 25, 812-817
48. W. D. Wulff, D. C. Yang, J. Am. Chem. Soc. 1984, 106, 7565-7567.
49. J. Barluenga, M. A. Fernández-Rodríguez, E. Aguilar, F. Fernández-Marí, B. Olano, A. Salinas, Chem. Eur. J. 2001, 7, 3533-3544.
50. G. Erker, F. Sosna, Organometallics 1990, 9, 1949-1953
51. C. M. Lukehart, J. V. Zeile, J. Organomet. Chem. 1975, 97, 421-428.
52. C. P. Casey, T. J. Burkhardt, C. A. Bunnell, J. C. Calabrese, J. Am. Chem. Soc. 1977, 99, 2127-2134.
53. A. M. Lluch, L. Jordi, F. Sánchez-Baeza, S. Ricart, F. Camps, A. Messeguer, J. M. Moretó, Tetrahedron Lett. 1992, 33, 3021-3022.
54. P. Quayle, S. Rahman, E. Ward, M. Lucy, J. Herbert, Tetrahedron Lett. 1994, 35, 3801-3804
55. K. H. Dötz, B. Fügen-Köster, D. Neugebauer, J. Organomet. Chem. 1979, 182, 489-498
56. C. P. Casey, R. A. Boggs, R. L. Anderson, J. Am. Chem. Soc. 1972, 94, 8947-8949.
57. D. Perdicchia, E. Licandro, S. Maiorana, B. Vandoni, C. Baldoli, Org. Lett. 2002, 4, 827-830.
58. R. Neidlein, S. Gurtler, Synthesis 1995, 325-329
59. R. Aumann, J. Schroeder, H. Heinen, Chem. Ber. 1990, 123, 1369-1374.
60. E. Licandro, S. Maiorana, A. Papagni, P. Hellier, L. Capella, A. Persoons, S. Houbrechts, J. Organomet. Chem. 1999, 583, 111-119
61. R. B. Silverman, R. A. Olofson, Chem. Commun. (London) 1968, 1313-1313.
62. J. Barluenga, F. Andina, M. A. Fernández-Rodríguez, P. García-García, I. Merino, E. Aguilar, J. Org. Chem. 2004, 69, 7352-7354.
63. J. Smidt, W. Hafner, R. Jira, J. Sedlmeier, R. Sieber, R. Rüttinger, H. Kojer, Angew. Chem. 1959, 71, 176-182
64. R. Jira, Angew. Chem. 2009, 121, 9196-9199
65. Angew. Chem. Int. Ed. 2009, 48, 9034-9037
66. J. A. Keith, P. M. Henry, Angew. Chem. 2009, 121, 9200-9212
67. Angew. Chem. Int. Ed. 2009, 48, 9038-9049
68. B. J. Anderson, J. A. Keith, M. S. Sigman, J. Am. Chem. Soc. 2010, 132, 11872-11874
69. R. I. McDonald, G. Liu, S. S. Stahl, Chem. Rev. 2011, 111, 2981-3019.
70. J. D. Lou, Z. N. Xu, Tetrahedron Lett. 2002, 43, 8843-8844
71. J. D. Lou, X. Y. Yu, Oxid. Commun. 1997, 20, 284-285
72. J. D. Lou, J. Chem. Res., Synop. 1997, 206-206
73. L. T. Sandborn, Org. Synth. 1941, 1, 340-341
74. R. O. Hutchins, N. R. Natale, W. J. Cook, J. Ohr, Tetrahedron Lett. 1977, 18, 4167-4169
75. L. F. Fieser, M. Fieser, Reagents for Organic Synthesis Vol. 1, Wiley, New York, 1967, pp. 144-147.
76. M. Hunsen, Synthesis 2005, 2487-2490
77. J. Muzart, Chem. Rev. 1992, 92, 113-140.
78. B. A. Anderson, W. D. Wulff, A. Rham, J. Am. Chem. Soc. 1993, 115, 4602-4611
79. W. D. Wulff, D. C. Yang, J. Am. Chem. Soc. 1983, 105, 6726-6727
80. E. O. Fischer, S. Walz, G. Kneis, F. R. Kreissl, Chem. Ber. 1977, 110, 1651-1658.
81. B. P. Taduri, S. M. A. Sohel, H.-M. Cheng, G.-Y. Lin, R.-S. Liu, Chem. Commun. 2007, 2530-2532.
82. J. Swanston, in Ullmann's Encyclopedia of Industrial Chemistry (Vol. 36), Wiley-VCH, Weinheim, 2006, pp. 657-658 (Thiophene)
83. L. Aurelio, H. Figler, B. L. Flynn, J. Linden, P. J. Scammells, Bioorg. Med. Chem. 2008, 16, 1319-1327
84. R. Romagnoli, P. G. Baraldi, M. D. Carrion, C. L. Cara, O. Cruz-Lopez, M. A. Iaconinoto, D. Preti, J. C. Shryock, A. R. Moorman, F. Vincentzi, K. Varani, P. A. Borea, J. Med. Chem. 2008, 51, 5875-5879.
85. J. Roncali, Chem. Rev. 1992, 92, 711-738
86. T. V. Thang, C. Cougnon, J. Electroanal. Chem. 2011, 657, 79-83
87. J. Frisch, A. Vollmer, J. P. Rabe, N. Koch, Org. Electron. 2011, 12, 916-922.
88. G. Li, E. Wang, H. Chen, H. Li, Y. Liu, P. Wang, Tetrahedron 2008, 64, 9033-9043.
89. M. A. Esteruelas, F. Liu, E. Oñate, E. Sola, B. Zeier, Organometallics 1997, 16, 2919-2928.
90. W. G. Duncan, W. T. Colwell, C. R. Scott, and, D. W. Henry, J. Med. Chem. 1968, 11, 1221-1223.
91. B. P. Das, J. A. Campbell, F. B. Samples, R. A. Wallace, L. K. Whisenant, R. W. Woodard, D. W. Boykin Jr., J. Med. Chem. 1972, 15, 370-374.
92. S. L. Jain, B. Sain, Chem. Commun. 2002, 1040-1041.
93. V. L. Pecoraro, M. J. Baldwin, A. Gelasco, Chem. Rev. 1994, 94, 807-826
94. E. A. Lewis, W. B. Tolman, Chem. Rev. 2004, 104, 1047-1076
95. M. Costas, M. P. Mehn, M. P. Jensen, J. Lawrence Que, Chem. Rev. 2004, 104, 939-986
96. S. S. Stahl, Angew. Chem. 2004, 116, 3480-3501
97. Angew. Chem. Int. Ed. 2004, 43, 3400-3420
98. M. Suzuki, Acc. Chem. Res. 2007, 40, 609-617.
99. M. E. N. Clemente, P. J. Saavedra, M. C. Vásquez, M. A. Paz-Sandoval, Organometallics 2002, 21, 592-605
100. G. Jia, W. S. Ng, H. S. Chu, W.-T. Wong, N.-T. Yu, I. D. Williams, Organometallics 1999, 18, 3597-3602.
101. J. Xiao, X. Li, Angew. Chem. 2011, 123, 7364-7375
102. Angew. Chem. Int. Ed. 2011, 50, 7226-7236
103. L. Ye, L. Cui, G. Zhang, L. Zhang, J. Am. Chem. Soc. 2010, 132, 3258-3259
104. L. Ye, W. He, L. Zhang, J. Am. Chem. Soc. 2010, 132, 8550-8551.
105. E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934
106. Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858
107. H. Werner, A. Stark, P. Steinert, C. Grünwald, J. Wolf, Chem. Ber. 1995, 128, 49-62
108. M. E. Bruin, E. P. Kündig, Chem. Commun. 1998, 2635-2636
109. T. Matsubara, N. Koga, D. G. Musaev, K. Morokuma, J. Am. Chem. Soc. 1998, 120, 12692-12693
110. T. Matsubara, N. Koga, D. G. Musaev, K. Morokuma, Organometallics 2000, 19, 2318-2329.
111. B. Martin-Matute, J. B. Aberg, M. Edin, J. E. Backvall, Chem. Eur. J. 2007, 13, 6063-6072
112. T. Fukuyama, T. Doi, S. Minamino, S. Omura, I. Ryu, Angew. Chem. 2007, 119, 5655-5657
113. Angew. Chem. Int. Ed. 2007, 46, 5559-5561
114. W. Baratta, K. Siega, P. Rigo, Chem. Eur. J. 2007, 13, 7479-7486
115. A. J. Johansson, E. Zuidema, C. Bolm, Chem. Eur. J. 2010, 16, 13487-13499.
116. C.-P. Chung, C.-C. Chen, Y.-C. Lin, Y.-H. Liu, Y. Wang, J. Am. Chem. Soc. 2009, 131, 18366-18375.
117. M. I. Bruce, R. C. Wallis, Aust. J. Chem. 1979, 32, 1471-1485
118. I. D. G. Watson, S. Ritter, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 2056-2057
119. A. P. Shaw, J. R. Norton, D. Buccella, L. A. Sites, S. S. Kleinbach, D. A. Jarem, K. M. Bocage, C. Nataro, Organometallics 2009, 28, 3804-3814.
120. M. I. Bruce, I. R. Butler, W. R. Cullen, G. A. Koutsantonis, M. R. Snow, E. R. T. Tiekink, Aust. J. Chem. 1988, 41, 963-969.
121. The SADABS program is based on the method developed by Blessing, see:, R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-38.
122. SHELXTL: Structure Analysis Program, version 5.04; Siemens Industrial Automation Inc., Madison, 1995.