Ruthenium-catalyzed cycloadditions of 1-haloalkynes with nitrile oxides and organic azides: Synthesis of 4-haloisoxazoles and 5-halotriazoles

Chemistry - A European Journal

Volumn 20, Issue 35, 2014, Pages 11101-11110

  Oakdale, James S ^a   Sit, Rakesh K ^a   Fokin, Valery V ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

alkynes; cycloadditions; halides; regioselectivity; ruthenium

Indexed keywords

AMIDES; CATALYSIS; CHLORINE COMPOUNDS; HYDROCARBONS; KETONES; NITROGEN COMPOUNDS; NITROGEN OXIDES; REGIOSELECTIVITY;

ALKYNES; CYCLOADDITIONS; CYCLOPENTADIENYLS; HALIDES; PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS; PENTAMETHYLCYCLOPENTADIENYL; POST-FUNCTIONALIZATION; ROOM TEMPERATURE;

RUTHENIUM;

EID: 84906785778     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201402559     Document Type: Article

References (122)

1. L. Zhang, X. Chen, P. Xue, H. H. Y. Sun, I. D. Williams, K. B. Sharpless, V. V. Fokin, G. Jia, J. Am. Chem. Soc. 2005, 127, 15998-15999
2. M. M. Majireck, S. M. Weinreb, J. Org. Chem. 2006, 71, 8680-8683
3. L. K. Rasmussen, B. C. Boren, V. V. Fokin, Org. Lett. 2007, 9, 5337-5339
4. B. C. Boren, S. Narayan, L. K. Rasmussen, L. Zhang, H. Zhao, Z. Lin, G. Jia, V. V. Fokin, J. Am. Chem. Soc. 2008, 130, 8923-8930.
5. S. Grecian, V. V. Fokin, Angew. Chem. 2008, 120, 8409-8411
6. Angew. Chem. Int. Ed. 2008, 47, 8285-8287.
7. A. Qin, J. W. Y. Lam, C. K. W. Jim, L. Zhang, J. Yan, M. Häussler, J. Liu, Y. Dong, D. Liang, E. Chen, G. Jia, B. Z. Tang, Macromolecules 2008, 41, 3808-3822
8. A. Tam, U. Arnold, M. B. Soellner, R. T. Raines, J. Am. Chem. Soc. 2007, 129, 12670-12671
9. H. Nulwala, K. Takizawa, A. Odukale, A. Khan, R. J. Thibault, B. R. Taft, B. H. Lipshutz, C. J. Hawker, Macromolecules 2009, 42, 6068-6074
10. M. Empting, O. Avrutina, R. Meusinger, S. Fabritz, M. Reinwarth, M. Biesalski, S. Voigt, G. Buntkowsky, H. Kolmar, Angew. Chem. 2011, 123, 5313-5317
11. Angew. Chem. Int. Ed. 2011, 50, 5207-5211
12. J.-M. Kee, B. Villani, L. R. Carpenter, T. W. Muir, J. Am. Chem. Soc. 2010, 132, 14327-14329
13. M. Tischler, D. Nasu, M. Empting, S. Schmelz, D. W. Heinz, P. Rottmann, H. Kolmar, G. Buntkowsky, D. Tietze, O. Avrutina, Angew. Chem. 2012, 124, 3768-3772
14. Angew. Chem. Int. Ed. 2012, 51, 3708-3712
15. W. S. Horne, C. A. Olsen, J. M. Beierle, A. Montero, M. R. Ghadiri, Angew. Chem. 2009, 121, 4812-4818
16. Angew. Chem. Int. Ed. 2009, 48, 4718-4724.
17. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
18. Angew. Chem. Int. Ed. 2002, 41, 2596-2599
19. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
20. Internal alkynes here refer to alkynes featuring carbon substituents on each acetylenic carbon atom.
21. M. Juricek, P. H. J. Kouwer, A. E. Rowan, Chem. Commun. 2011, 47, 8740-8749.
22. J. E. Hein, V. V. Fokin, Chem. Soc. Rev. 2010, 39, 1302-1315
23. M. Meldal, C. W. Tornøe, Chem. Rev. 2008, 108, 2952-3015.
24. S. Chuprakov, S. W. Kwok, V. V. Fokin, J. Am. Chem. Soc. 2013, 135, 4652-4655
25. N. Selander, B. T. Worrell, S. Chuprakov, S. Velaparthi, V. V. Fokin, J. Am. Chem. Soc. 2012, 134, 14670-14673
26. S. Chuprakov, J. A. Malik, M. Zibinsky, V. V. Fokin, J. Am. Chem. Soc. 2011, 133, 10352-10355
27. T. Horneff, S. Chuprakov, N. Chernyak, V. Gevorgyan, V. V. Fokin, J. Am. Chem. Soc. 2008, 130, 14972-14974.
28. e. M. T. M. V. D. Pinho, Curr. Org. Chem. 2005, 9, 925-958
29. J. B. Sperry, D. L. Wright, Curr. Opin. Drug Discovery Dev. 2005, 8, 723-740.
30. P. G. Baraldi, A. Barco, S. Benetti, F. Moroder, G. P. Pollini, D. Simoni, J. Org. Chem. 1983, 48, 1297-1302.
31. M. Nitta, T. Kobayashi, J. Chem. Soc. Perkin Trans. 1 1985, 1401-1406.
32. A. I. Kotyatkina, V. N. Zhabinsky, V. A. Khripach, Russ. Chem. Rev. 2001, 70, 641-653
33. K. C. Coffman, T. A. Palazzo, T. P. Hartley, J. C. Fettinger, D. J. Tantillo, M. J. Kurth, Org. Lett. 2013, 15, 2062-2065.
34. P. G. Baraldi, A. Barco, S. Benetti, G. P. Pollini, D. Simoni, Synthesis 1987, 857-869
35. A. L. Smith, E. N. Pitsinos, C. K. Hwang, Y. Mizuno, H. Saimoto, G. R. Scarlato, T. Suzuki, K. C. Nicolaou, J. Am. Chem. Soc. 1993, 115, 7612-7624
36. B. Heasley, Angew. Chem. 2011, 123, 8624-8627
37. Angew. Chem. Int. Ed. 2011, 50, 8474-8477.
38. T. V. Hansen, P. Wu, V. V. Fokin, J. Org. Chem. 2005, 70, 7761-7764.
39. J. E. Hein, J. C. Tripp, L. B. Krasnova, K. B. Sharpless, V. V. Fokin, Angew. Chem. 2009, 121, 8162-8165
40. Angew. Chem. Int. Ed. 2009, 48, 8018-8021.
41. P.-A. Fournier, M. Arbour, E. Cauchon, A. Chen, A. Chefson, Y. Ducharme, J.-P. Falgueyret, S. Gagné, E. Grimm, Y. Han, R. Houle, P. Lacombe, J.-F. Lévesque, D. MacDonald, B. Mackay, D. McKay, M. D. Percival, Y. Ramtohul, R. St-Jacques, S. Toulmond, Bioorg. Med. Chem. Lett. 2012, 22, 2670-2674
42. R. Palin, L. Abernethy, N. Ansari, K. Cameron, T. Clarkson, M. Dempster, D. Dunn, A.-M. Easson, D. Edwards, J. Maclean, K. Everett, H. Feilden, K.-K. Ho, S. Kultgen, P. Littlewood, D. McArthur, D. McGregor, H. McLuskey, I. Neagu, S. Neale, L.-A. Nisbet, M. Ohlmeyer, Q. Pham, P. Ratcliffe, Y. Rong, A. Roughton, M. Sammons, R. Swanson, H. Tracey, G. Walker, Bioorg. Med. Chem. Lett. 2011, 21, 892-898
43. J. He, L. Feng, J. Li, R. Tao, F. Wang, X. Liao, Q. Sun, Q. Long, Y. Ren, J. Wan, H. He, Bioorg. Med. Chem. 2012, 20, 1665-1670.
44. B. T. Worrell, J. E. Hein, V. V. Fokin, Angew. Chem. 2012, 124, 11961-11964
45. Angew. Chem. Int. Ed. 2012, 51, 11791-11794
46. H. A. Michaels, J. T. Simmons, R. J. Clark, L. Zhu, J. Org. Chem. 2013, 78, 5038-5044.
47. B. H. M. Kuijpers, G. C. T. Dijkmans, S. Groothuys, P. J. L. M. Quaedflieg, R. H. Blaauw, F. L. van Delft, F. P. J. T. Rutjes, Synlett 2005, 3059-3062
48. J. García-Álvarez, J. Diez, J. Gimeno, Green Chem. 2010, 12, 2127-2130
49. J. García-Álvarez, J. Diez, J. Gimeno, F. J. Suárez, C. Vincent, Eur. J. Inorg. Chem. 2012, 5854-5863
50. E. Rasolofonjatovo, S. Theeramunkong, A. Bouriaud, S. Kolodych, M. Chaumontet, F. Taran, Org. Lett. 2013, 15, 4698-4701.
51. W. S. Brotherton, R. J. Clark, L. Zhu, J. Org. Chem. 2012, 77, 6443-6455
52. V. Malnuit, M. Duca, A. Manout, K. Bougrin, R. Benhida, Synlett 2009, 2123-2126
53. Y.-M. Wu, J. Deng, Y. Li, Q.-Y. Chen, Synthesis 2005, 1314-1318
54. B. Wang, J. Zhang, X. Wang, N. Liu, W. Chen, Y. Hu, J. Org. Chem. 2013, 78, 10519-10523
55. R. Yan, K. Sander, E. Galante, V. Rajkumar, A. Badar, M. Robson, E. El-Emir, M. F. Lythgoe, R. B. Pedley, E. Årstad, J. Am. Chem. Soc. 2012, 134, 703-709.
56. Y. Zhou, T. Lecourt, L. Micouin, Angew. Chem. 2010, 122, 2661-2664
57. Angew. Chem. Int. Ed. 2010, 49, 2607-2610.
58. B. T. Worrell, S. P. Ellery, V. V. Fokin, Angew. Chem. 2013, 125, 13275-13279
59. Angew. Chem. Int. Ed. 2013, 52, 13037-13041.
60. A. Krasiński, V. V. Fokin, K. B. Sharpless, Org. Lett. 2004, 6, 1237-1240.
61. E. Lieber, T. S. Chao, C. N. R. Rao, Can. J. Chem. 1959, 37, 118-119
62. G. LAbbé, L. Beenaerts, Tetrahedron 1989, 45, 749-756.
63. J. Huang, S. J. F. Macdonald, J. P. A. Harrity, Chem. Commun. 2009, 436-438.
64. A. Darwish, M. Blacker, N. Janzen, S. M. Rathmann, S. Czorny, S. M. Hillier, J. L. Joyal, J. W. Babich, J. F. Valliant, ACS Med. Chem. Lett. 2012, 3, 313-316.
65. L. Claisen, O. Lowman, Ber. Dtsch. Chem. Ges. 1888, 21, 1149-1157.
66. J. P. Waldo, R. C. Larock, J. Org. Chem. 2007, 72, 9643-9647
67. J. P. Waldo, R. C. Larock, Org. Lett. 2005, 7, 5203-5205
68. O. Debleds, E. Gayon, E. Ostaszuk, E. Vrancken, J.-M. Campagne, Chem. Eur. J. 2010, 16, 12207-12213.
69. D. Chiarino, M. Napoletano, A. Sala, J. Heterocycl. Chem. 1987, 24, 43-46.
70. M. L. McIntosh, M. R. Naffziger, B. O. Ashburn, L. N. Zakharov, R. G. Carter, Org. Biomol. Chem. 2012, 10, 9204-9213
71. J. A. Crossley, D. L. Browne, J. Org. Chem. 2010, 75, 5414-5416
72. Y.-Y. Ku, T. Grieme, P. Sharma, Y.-M. Pu, P. Raje, H. Morton, S. King, Org. Lett. 2001, 3, 4185-4187.
73. T. Kitamura, Y. Mansei, Y. Fujiwara, J. Organomet. Chem. 2002, 646, 196-199
74. P. J. Stang, P. Murch, Tetrahedron Lett. 1997, 38, 8793-8794
75. E. Kotali, A. Varvoglis, A. Bozopoulos, J. Chem. Soc. Perkin Trans. 1 1989, 827-832.
76. K. Takenaka, S. Nakatsuka, T. Tsujihara, P. S. Koranne, H. Sasai, Tetrahedron: Asymmetry 2008, 19, 2492-2496
77. J. J. Letourneau, C. Riviello, M. H. J. Ohlmeyer, Tetrahedron Lett. 2007, 48, 1739-1743
78. P. D. Stein, D. M. Floyd, S. Bisaha, J. Dickey, R. N. Girotra, J. Z. Gougoutas, M. Kozlowski, V. G. Lee, E. C. K. Liu, J. Med. Chem. 1995, 38, 1344-1354.
79. Z.-X. Yu, P. Caramella, K. N. Houk, J. Am. Chem. Soc. 2003, 125, 15420-15425
80. F. De Sarlo, J. Chem. Soc. Perkin Trans. 1 1974, 1951-1953.
81. The regiochemistry of the 4-haloisoxazole product was confirmed in two ways: 1) Compound 3 a was subjected to magnesium-halogen exchange with ethyl magnesium bromide followed by a subsequent proton quench with methanol to yield the parent 4-proto-isoxazole. Concurrently, the same compound was prepared for comparison purposes through the copper-catalyzed cycloaddition of alkyne 70 + hydroximoyl chloride 2. 2) An X-ray crystal structure of compound 8 was obtained. See the Supporting Information for experimental details.
82. C. J. Cavallito, J. Am. Chem. Soc. 1955, 77, 4159-4160.
83. H. Hofmeister, K. Annen, H. Laurent, R. Wiechert, Angew. Chem. 1984, 96, 720-722
84. Angew. Chem. Int. Ed. Engl. 1984, 23, 727-729.
85. Y. Sasson, O. W. Webster, J. Chem. Soc. Chem. Commun. 1992, 1200-1201.
86. The regiochemistry of the 5-halotriazole product was confirmed for compounds 5 c and 46 by magnesium-halogen exchange with ethyl magnesium bromide followed by subsequent quenching with methanol. For comparison purposes, the corresponding 5-proto derivatives were also prepared through CuAAC from 70 and the requisite azides. See the Supporting Information for experimental details.
87. Y. Carcenac, F. David-Quillot, M. Abarbri, A. Duchene, J. Thibonnet, Synthesis 2013, 45, 633-638
88. A. R. Bogdan, K. James, Org. Lett. 2011, 13, 4060-4063
89. J. Deng, Y.-M. Wu, Q.-Y. Chen, Synthesis 2005, 8, 2730-2738.
90. T. Haddad, R. Gershman, R. Dilis, D. Labaree, R. B. Hochberg, R. N. Hanson, Bioorg. Med. Chem. Lett. 2012, 22, 5999-6003.
91. S. Nahm, S. M. Weinreb, Tetrahedron Lett. 1981, 22, 3815-3818
92. S. Balasubramaniam, I. S. Aidhen, Synthesis 2008, 23, 3707-3738.
93. Y. Yamamoto, T. Arakawa, R. Ogawa, K. Itoh, J. Am. Chem. Soc. 2003, 125, 12143-12160.
94. Y. Yamamoto, K. Hattori, H. Nishiyama, J. Am. Chem. Soc. 2006, 128, 8336-8340
95. Y. Yamamoto, K. Hattori, Tetrahedron 2008, 64, 847-855
96. K. C. Nicolaou, J. Wang, Y. Tang, L. Botta, J. Am. Chem. Soc. 2010, 132, 11350-11363.
97. A. Allen, K. Villeneuve, N. Cockburn, E. Fatila, N. Riddell, W. Tam, Eur. J. Org. Chem. 2008, 4178-4192.
98. M. O. Albers, D. J. Robinson, A. Shaver, E. Singleton, Organometallics 1986, 5, 2199-2205.
99. P. J. Fagan, M. D. Ward, J. C. Calabrese, J. Am. Chem. Soc. 1989, 111, 1698-1719
100. D. Rondon, B. Chaudret, X. D. He, D. Labroue, J. Am. Chem. Soc. 1991, 113, 5671-5676
101. M. Jiménez-Tenorio, M. C. Puerta, P. Valerga, Eur. J. Inorg. Chem. 2004, 17-32.
102. J. A. Varela, L. Castedo, C. Saá, Org. Lett. 2003, 5, 2841-2844
103. J. A. Varela, L. Castedo, C. Saá, J. Org. Chem. 2003, 68, 8595-8598.
104. E. Rüba, R. Schmid, K. Kirchner, M. J. Calhorda, J. Organomet. Chem. 2003, 682, 204-211.
105. J. R. Sowa, R. J. Angelici, J. Am. Chem. Soc. 1991, 113, 2537-2544
106. P. G. Gassman, D. W. Macomber, J. W. Hershberger, Organometallics 1983, 2, 1470-1472.
107. P. G. Gassman, C. H. Winter, J. Am. Chem. Soc. 1988, 110, 6130-6135
108. P. G. Gassman, J. R. Sowa, M. G. Hill, K. R. Mann, Organometallics 1995, 14, 4879-4885.
109. M. D. Curtis, K. B. Shiu, W. M. Butler, J. C. Huffman, J. Am. Chem. Soc. 1986, 108, 3335-3343.
110. For examples of coordinatively unsaturated half-sandwich ruthenium(II) complexes, see
111. B. K. Campion, R. H. Heyn, T. D. Tilley, J. Chem. Soc. Chem. Commun. 1988, 278-280
112. T. J. Johnson, K. Folting, W. E. Streib, J. D. Martin, J. C. Huffman, S. A. Jackson, O. Eisenstein, K. G. Caulton, Inorg. Chem. 1995, 34, 488-499
113. J. Huang, H.-J. Schanz, E. D. Stevens, S. P. Nolan, Organometallics 1999, 18, 2370-2375.
114. P. G. Gassman, J. W. Mickelson, J. R. Sowa, J. Am. Chem. Soc. 1992, 114, 6942-6944.
115. Y. Imazaki, E. Shirakawa, R. Ueno, T. Hayashi, J. Am. Chem. Soc. 2012, 134, 14760-14763
116. A. Mercier, W. C. Yeo, J. Chou, P. D. Chaudhuri, G. Bernardinelli, E. P. Kundig, Chem. Commun. 2009, 5227-5229
117. H.-J. Zhang, B. Demerseman, Z. Xi, C. Bruneau, Eur. J. Inorg. Chem. 2008, 3212-3217.
118. L. P. Barthel-Rosa, J. R. Sowa, P. G. Gassman, J. Fischer, B. M. McCarty, S. L. Goldsmith, M. T. Gibson, J. H. Nelson, Organometallics 1997, 16, 1595-1603.
119. E. Boz, N. Ş. Tüzün, J. Organomet. Chem. 2013, 724, 167-176
120. M. Lamberti, G. C. Fortman, A. Poater, J. Broggi, A. M. Z. Slawin, L. Cavallo, S. P. Nolan, Organometallics 2012, 31, 756-767
121. D.-R. Hou, T.-C. Kuan, Y.-K. Li, R. Lee, K.-W. Huang, Tetrahedron 2010, 66, 9415-9420
122. Y.-B. Zhou, Z.-F. Ke, C.-Y. Zhao, Huaxue Xuebao 2006, 64, 2071-2078.