Rhodium(II)-catalyzed intramolecular cycloisomerizations of methylenecyclopropanes with N-Sulfonyl 1,2,3-Triazoles

Angewandte Chemie - International Edition

Volumn 53, Issue 26, 2014, Pages 6645-6649

  Chen, Kai ^a   Zhu, Zi Zhong ^a   Zhang, Yong Sheng ^b   Tang, Xiang Ying ^b   Shi, Min ^a,b  

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

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

carbenes; isomerization; nitrogen heterocycles; rhodium; small ring systems

Indexed keywords

CATALYSIS; ISOMERIZATION; ORGANIC COMPOUNDS; PROPANE; REACTION INTERMEDIATES; SYNTHESIS (CHEMICAL);

1 ,2 ,3-TRIAZOLES; CARBENES; CYCLOISOMERIZATIONS; DIVERGENT SYNTHESIS; METHYLENECYCLOPROPANES; NITROGEN HETEROCYCLES; REACTION PATHWAYS; SMALL RING SYSTEMS;

RHODIUM;

EID: 84903268945     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201402803     Document Type: Article

References (109)

1. M. Shi, J.-M. Lu, Y. Wei, L.-X. Shao, Acc. Chem. Res. 2012, 45, 641-652
2. M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117-3179
3. I. Nakamura, Y. Yamamoto, Adv. Synth. Catal. 2002, 344, 111-129
4. A. Brandi, S. Cicchi, F. M. Cordero, A. Goti, Chem. Rev. 2003, 103, 1213-1270
5. M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49-92
6. M. S. Baird, in Carbocyclic Three- and Four-Membered Ring Compounds, Vol.E17d (Ed.:, A. deMeijere,), Thieme, Stuttgart, 1997, pp. 2759-2779
7. H. Maeda, K. Mizuno, J. Synth. Org. Chem. Jpn. 2004, 62, 1014-1025
8. L.-X. Shao, M. Shi, Curr. Org. Chem. 2007, 11, 1135-1137
9. A. deMeijere, S. I. Kozhushkov, A. F. Khlebnikov, Top. Curr. Chem. 2000, 207, 89-147
10. A. deMeijere, S. I. A. Kozhushkov, Eur. J. Org. Chem. 2000, 3809-3822
11. A. deMeijere, S. I. Kozhushkov, T. Spath, M. vonSeebach, S. Lohr, H. Nuske, T. Pohomann, M. Es-Sayed, S. Bräse, Pure Appl. Chem. 2000, 72, 1745-1756
12. E. Smolensky, M. Kapon, M. S. Eisen, Organometallics 2007, 26, 4510-4527
13. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320-330
14. M. Cheeseman, I. R. Davies, P. Axe, A. L. Johnson, S. D. Bull, Org. Biomol. Chem. 2009, 7, 3537-3548
15. M. Shi, L.-X. Shao, J.-M. Lu, Y. Wei, K. Mizuno, H. Maeda, Chem. Rev. 2010, 110, 5883-5913
16. H. Pellissier, Tetrahedron 2010, 66, 8341-8375
17. G. Audran, H. Pellissier, Adv. Synth. Catal. 2010, 352, 575-608
18. A. Masarwa, I. Marek, Chem. Eur. J. 2010, 16, 9712-9721
19. L. Yu, R. Guo, Org. Prep. Proc. Int. 2011, 43, 209-259.
20. G.-Q. Tian, M. Shi, Org. Lett. 2007, 9, 4917-4920
21. L.-X. Shao, Y.-X. Li, M. Shi, Chem. Eur. J. 2007, 13, 862-869
22. M. Lautens, W. Han, J. Am. Chem. Soc. 2002, 124, 6312-6316
23. M. Lautens, W. Han, J. H. Liu, J. Am. Chem. Soc. 2003, 125, 4028-4029
24. M. E. Scott, M. Lautens, Org. Lett. 2005, 7, 3045-3047
25. S. Simaan, A. Masarwa, P. Bertus, I. Marek, Angew. Chem. 2006, 118, 4067-4069
26. Angew. Chem. Int. Ed. 2006, 45, 3963-3965
27. A. Masarwa, A. Stanger, I. Marek, Angew. Chem. 2007, 119, 8185-8188
28. Angew. Chem. Int. Ed. 2007, 46, 8039-8042
29. M. E. Scott, Y. Bethuel, M. Lautens, J. Am. Chem. Soc. 2007, 129, 1482-1483
30. C. Taillier, M. Lautens, Org. Lett. 2007, 9, 591-593
31. M. E. Scott, M. Lautens, J. Org. Chem. 2008, 73, 8154-8162
32. S. Simaan, A. F. G. Goldberg, S. Rosset, I. Marek, Chem. Eur. J. 2010, 16, 774-778
33. Z. Zhang, M. Shi, Tetrahedron Lett. 2011, 52, 6541-6544
34. K. Chen, M. Jiang, Z. Zhang, Y. Wei, M. Shi, Eur. J. Org. Chem. 2011, 7189-7193
35. D.-H. Zhang, Y. Wei, M. Shi, Chem. Eur. J. 2012, 18, 7026-7029
36. L. Ackermann, S. I. Kozhushkov, D. S. Yufit, Chem. Eur. J. 2012, 18, 12068-12077
37. K. Chen, Z. Zhang, Y. Wei, M. Shi, Chem. Commun. 2012, 48, 7696-7698
38. K. Chen, R. Sun, Q. Xu, Y. Wei, M. Shi, Org. Biomol. Chem. 2013, 11, 3949-3953
39. D.-H. Zhang, X.-Y. Tang, Y. Wei, M. Shi, Chem. Eur. J. 2013, 19, 13668-13673
40. N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123-8124
41. C. Aïssa, A. Fürstner, J. Am. Chem. Soc. 2007, 129, 14836-14837
42. M. Shi, L.-P. Liu, J. Tang, J. Am. Chem. Soc. 2006, 128, 7430-7431
43. A. Fürstner, C. Aïssa, J. Am. Chem. Soc. 2006, 128, 6306-6307.
44. N. V. Yashin, E. B. Averina, Y. K. Grishin, T. S. Kuznetsova, N. S. Zefirov, Synthesis 2006, 279-284
45. T. Kurahashi, Y. T. Wu, K. Meindl, S. Rühl, A. deMeijere, Synlett 2005, 805-808
46. K. Kamikawa, Y. Shimizu, S. Takemoto, H. Matsuzaka, Org. Lett. 2006, 8, 4011-4014
47. Y. Liang, L. Jiao, Y. Wang, Y. Chen, L. Ma, J. Xu, S. Zhang, Z.-X. Yu, Org. Lett. 2006, 8, 5877-5879
48. W. Li, M. Shi, Tetrahedron 2007, 63, 11016-11020
49. D.-H. Zhang, Y. Wei, M. Shi, Eur. J. Org. Chem. 2011, 4940-4944.
50. E. J. Yoo, M. Ahlquist, S. H. Kim, I. Bae, V. V. Fokin, K. B. Sharpless, S. Chang, Angew. Chem. 2007, 119, 1760-1763
51. Angew. Chem. Int. Ed. 2007, 46, 1730-1733
52. J. Raushel, V. V. Fokin, Org. Lett. 2010, 12, 4952-4955
53. Y. Liu, X. Wang, J. Xu, Q. Zhang, Y. Zhao, Y. Hu, Tetrahedron 2011, 67, 6294-6299.
54. B. Chattopadhyay, V. Gevorgyan, Angew. Chem. 2012, 124, 886-896
55. Angew. Chem. Int. Ed. 2012, 51, 862-872
56. A. V. Gulevich, V. Gevorgyan, Angew. Chem. 2013, 125, 1411-1413
57. Angew. Chem. Int. Ed. 2013, 52, 1371-1373.
58. S. Chuprakov, F. W. Hwang, V. Gevorgyan, Angew. Chem. 2007, 119, 4841-4843
59. Angew. Chem. Int. Ed. 2007, 46, 4757-4759
60. T. Horneff, S. Chuprakov, N. Chernyak, V. Gevorgyan, V. V. Fokin, J. Am. Chem. Soc. 2008, 130, 14972-14974
61. T. Miura, M. Yamauchi, M. Murakami, Chem. Commun. 2009, 1470-1471
62. B. Chattopadhyay, V. Gevorgyan, Org. Lett. 2011, 13, 3746-3749
63. M. Zibinsky, V. V. Fokin, Angew. Chem. 2013, 125, 1547-1550
64. Angew. Chem. Int. Ed. 2013, 52, 1507-1510
65. S. Chuprakov, S. W. Kwok, V. V. Fokin, J. Am. Chem. Soc. 2013, 135, 4652-4655
66. B. T. Parr, S. A. Green, H. M. L. Davies, J. Am. Chem. Soc. 2013, 135, 4716-4718
67. J. E. Spangler, H. M. L. Davies, J. Am. Chem. Soc. 2013, 135, 6802-6805
68. Y. Shi, V. Gevorgyan, Org. Lett. 2013, 15, 5394-5396.
69. Comprehensive Heterocyclic Chemistry II (Ed.:, C.W. Bird,), Pergamon, Oxford, 1996.
70. S. Chuprakov, S. W. Kwok, L. Zhang, L. Lercher, V. V. Fokin, J. Am. Chem. Soc. 2009, 131, 18034-18035
71. N. Grimster, L. Zhang, V. V. Fokin, J. Am. Chem. Soc. 2010, 132, 2510-2511
72. J. S. Alford, H. M. L. Davies, Org. Lett. 2012, 14, 6020-6023
73. J. C. Culhane, V. V. Fokin, Org. Lett. 2011, 13, 4578-4580.
74. S. Chuprakov, J. A. Malik, M. Zibinsky, V. V. Fokin, J. Am. Chem. Soc. 2011, 133, 10352-10355.
75. T. Miura, T. Biyajima, T. Fujii, M. Murakami, J. Am. Chem. Soc. 2012, 134, 194-196
76. T. Miura, T. Tanaka, T. Biyajima, A. Yada, M. Murakami, Angew. Chem. 2013, 125, 3975-3978
77. Angew. Chem. Int. Ed. 2013, 52, 3883-3886
78. S. Chuprakov, B. T. Worrell, N. Selander, R. K. Sit, V. V. Fokin, J. Am. Chem. Soc. 2014, 136, 195-202.
79. N. Selander, B. T. Worrell, S. Chuprakov, S. Velaparthi, V. V. Fokin, J. Am. Chem. Soc. 2012, 134, 14670-14673.
80. N. Selander, B. T. Worrell, V. V. Fokin, Angew. Chem. 2012, 124, 13231-13234
81. Angew. Chem. Int. Ed. 2012, 51, 13054-13057
82. T. Miura, Y. Funakoshi, M. Morimoto, T. Biyajima, M. Murakami, J. Am. Chem. Soc. 2012, 134, 17440-17443
83. J. S. Alford, J. E. Spangler, H. M. L. Davies, J. Am. Chem. Soc. 2013, 135, 11712-11715
84. E. E. Schultz, R. Sarpong, J. Am. Chem. Soc. 2013, 135, 4696-4699
85. T. Miura, Y. Funakoshi, M. Murakami, J. Am. Chem. Soc. 2014, 136, 2272-2275.
86. S. Li, Y. Luo, J. Wu, Org. Lett. 2011, 13, 3190-3913.
87. D. Lucet, T. L. Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772
88. Angew. Chem. Int. Ed. 1998, 37, 2580-2627
89. A. Marquet, Pure Appl. Chem. 1993, 65, 1249-1252
90. P. Kulanthaivel, Y. F. Hallock, C. Boros, S. M. Hamilton, W. P. Janzen, L. M. Ballas, C. R. Loomis, J. B. Jiang, B. Katz, J. R. Steiner, J. Clardy, J. Am. Chem. Soc. 1993, 115, 6452-6453
91. J. Reedijk, Chem. Commun. 1996, 801-806.
92. E. Lee-Ruff, G. Mladenova, Chem. Rev. 2003, 103, 1449-1483
93. J. C. Namyslo, D. Kaufmann, Chem. Rev. 2003, 103, 1485-1538
94. J. Dai, J. I. Jiménez, M. Kelly, P. G. Williams, J. Org. Chem. 2010, 75, 2399-2402
95. R. P. Walker, D. J. Faulkner, D. VanEngen, J. Clardy, J. Am. Chem. Soc. 1981, 103, 6772-6773
96. F. P. Lee, Y. C. Chen, J. J. Chen, I. L. Tsai, I. S. Chen, Helv. Chim. Acta 2004, 87, 463-468.
97. R. B. Setlow, Science 1966, 153, 379-386.
98. CCDC936225 (2a) and 972728 (3a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
99. CCDC995120 (2r), 996791 (2s) and 995454 (2t) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
100. J. D. Winkler, R. D. Scott, P. G. Williard, J. Am. Chem. Soc. 1990, 112, 8971-8975
101. Y. Kwak, J. D. Winkler, J. Am. Chem. Soc. 2001, 123, 7429-7430
102. J. D. White, D. C. Ihle, Org. Lett. 2006, 8, 1081-1084
103. P. Chen, P. J. Carroll, S. M. Sieburth, Org. Lett. 2009, 11, 4540-4543.
104. G. Cignarella, E. Occelli, G. Cristiani, L. Paduano, E. Testa, J. Med. Chem. 1963, 6, 764-766
105. G. Cignarella, E. Occelli, E. Testa, J. Med. Chem. 1965, 8, 326-331
106. S. Pichlmair, K. Mereiter, U. Jordis, Tetrahedron Lett. 2004, 45, 1481-1483
107. C. J. Dinsmore, J. M. Bergman, M. J. Bogusky, J. C. Culberson, K. A. Hamilton, S. L. Graham, Org. Lett. 2001, 3, 865-868
108. E. Schipper, W. R. Boehme, J. Org. Chem. 1961, 26, 3599-3602.
109. CCDC977007 (7a) and 987877 (9a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.