Ring expansion and rearrangements of rhodium(II) azavinyl carbenes

Angewandte Chemie - International Edition

Volumn 51, Issue 52, 2012, Pages 13054-13057

  Selander, Nicklas ^a   Worrell, Brady T ^a   Fokin, Valery V ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Click chemistry; Heterocycles; Rearrangement; Rhodium(II) catalysis; Ring expansion

Indexed keywords

CARBENES; CARBOCYCLIC RINGS; CLICK CHEMISTRY; DIAZO COMPOUNDS; DRUG MOLECULES; ENAMINONES; HETEROCYCLES; NATURAL PRODUCTS; ORGANIC SYNTHESIS; PHARMACEUTICAL RESEARCH; REARRANGEMENT; REARRANGEMENT REACTIONS; RING EXPANSION; ROBUST METHODS; SIMPLE METHOD;

CATALYSIS; DRUG PRODUCTS; KETONES; OLEFINS; ORGANIC COMPOUNDS; RHODIUM; SYNTHESIS (CHEMICAL);

RHODIUM COMPOUNDS;

ALKENE; CARBENE; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; METHANE; RHODIUM; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CLICK CHEMISTRY; STEREOISOMERISM;

ALKENES; CATALYSIS; CLICK CHEMISTRY; HETEROCYCLIC COMPOUNDS; METHANE; RHODIUM; STEREOISOMERISM; TRIAZOLES;

EID: 84871977552     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201207820     Document Type: Article

References (42)

1. Rhodium(II)-catalyzed ring expansions: a) A. Padwa, Y. S. Kulkarni, Z. Zhang, J. Org. Chem. 1990, 55, 4144
2. b) R. Pellicciari, B. Natalini, B. M. Sadeghpour, M. Marinozzi, J. P. Snyder, B. L. Williamson, J. T. Kuethe, A. Padwa, J. Am. Chem. Soc. 1996, 118, 1
3. c) D. Damour, A. Renaudon, S. Mignani, Synlett 1995, 111
4. d) S. Chen, Y. Zhao, J. Wang, Synthesis 2006, 1705
5. e) H. Xu, W. Zhang, D. Shu, J. B. Werness, W. Tang, Angew. Chem. 2008, 120, 9065
6. Angew. Chem. Int. Ed. 2008, 47, 8933
7. for a recent example of a chiral Lewis acid catalyzed ring expansion, see: f) T. Hashimoto, Y. Naganawa, K. Maruoka, J. Am. Chem. Soc. 2011, 133, 8834
8. Rhodium(II)-catalyzed rearrangements: g) K. Nagao, M. Chiba, S.-W. Kim, Synthesis 1983, 197
9. h) K. Nagao, I. Yoshimura, M. Chiba, S.-W. Kim, Chem. Pharm. Bull. 1983, 31, 114
10. i) R. Pellicciari, B. Natalini, S. Cecchetti, R. Fringuelli, Steroids 1987, 49, 433
11. j) R. Baudouy, J. Core, L. Ruest, Tetrahedron 1987, 43, 1099
12. k) T. Ye, M. A. McKervey, Tetrahedron 1992, 48, 8007
13. l) S. Kanemasa, T. Kanai, T. Araki, E. Wada, Tetrahedron Lett. 1999, 40, 5055
14. m) M. Vitale, T. Lecourt, C. G. Sheldon, V. K. Aggarwal, J. Am. Chem. Soc. 2006, 128, 2524
15. W. Shi, F. Xiao, J. Wang, J. Org. Chem. 2005, 70, 4318.
16. a) L. Yet, Chem. Rev. 2000, 100, 2963
17. b) Y.-F. Wang, Q.-W. Shi, M. Dong, H. Kiyota, Y.-C. Gu, B. Cong, Chem. Rev. 2011, 111, 7652.
18. Recent uses of rhodium-catalyzed ring expansions in synthesis: a) P. Wender, N. Deschamps, R. Sun, Angew. Chem. 2006, 118, 4061
19. Angew. Chem. Int. Ed. 2006, 45, 3957
20. b) B. Frey, A. P. Wells, D. H. Rogers, L. N. Mander, J. Am. Chem. Soc. 1998, 120, 1914
21. c) J. L. Kane, K. M. Shea, A. L. Crombie, R. L. Danheiser, Org. Lett. 2001, 3, 1081
22. d) R. Liu, M. Zhang, T. P. Wyche, G. N. Winston-McPherson, T. S. Bugni, W. Tang, Angew. Chem. 2012, 124, 7621
23. Angew. Chem. Int. Ed. 2012, 51, 7503.
24. Recent uses of rhodium(II) azavinyl carbenes: a) T. Horneff, S. Chuprakov, N. Chernyak, V. Gevorgyan, V. V. Fokin, J. Am. Chem. Soc. 2008, 130, 14972
25. b) T. Miura, M. Yamauchi, M. Murakami, Chem. Commun. 2009, 1359
26. c) B. Chattopadhyay, V. Gevorgyan, Org. Lett. 2011, 13, 3746
27. d) S. Chuprakov, S. W. Kwok, L. Zhang, L. Lercher, V. V. Fokin, J. Am. Chem. Soc. 2009, 131, 18034
28. e) N. P. Grimster, L. Zhang, V. V. Fokin, J. Am. Chem. Soc. 2010, 132, 4870
29. f) S. Chuprakov, J. A. Malik, M. Zibinsky, V. V. Fokin, J. Am. Chem. Soc. 2011, 133, 10352
30. g) T. Miura, T. Biyajima, T. Fujii, M. Murakami, J. Am. Chem. Soc. 2012, 134, 194
31. h) N. Selander, B. T. Worrell, S. Chuprakov, S. Velaparthi, V. V. Fokin, J. Am. Chem. Soc. 2012, 134, 14670.
32. For a recent review of denitrogenative reactions of 1-sulfonyl triazoles, see: B. Chattopadhyay, V. Gevorgyan, Angew. Chem. 2012, 124, 886
33. Angew. Chem. Int. Ed. 2012, 51, 862.
34. Initial experiments were performed by Dr. Jessica Raushel
35. J. Raushel, Diss. Abstr. Int. B 2009, 69, 4763 (Ph.D Dissertation, The Scripps Research Institute, La Jolla, CA, 2009).
36. For a recent study of the ring expansion of 4-cyclopropyl-1-sulfonyl-1,2, 3-triazoles to substituted cyclobutenes under silvercatalyzed conditions, see: R. Liu, M. Zhang, G. Winston-McPherson, W. Tang, Chem. Commun. 2012, DOI: 10.1039/c2cc34609e.
37. J. Raushel, V. V. Fokin, Org. Lett. 2010, 12, 4952.
38. Selected applications of enaminones in synthesis: a) J. V. Greenhill, Chem. Soc. Rev. 1977, 6, 277
39. b) Z. A. Elassar, A. A. El-Dhair, Tetrahedron 2003, 59, 8463
40. c) B. Stanovnik, J. Svete, Chem. Rev. 2004, 104, 2433
41. d) K. B. Hansen, Y. Hsiao, F. Xu, N. Rivera, A. Clausen, M. Kubryk, S. Krska, T. Rosner, B. Simmons, J. Balsells, N. Ikemoto, Y. Sun, F. Spindler, C. Malan, E. J. J. Grabowski, J. D. Armstrong III, J. Am. Chem. Soc. 2009, 131, 8798.
42. While this manuscript was under review, the following account describing a similar transformation of 1-sulfonyl triazoles to substituted enaminones was published: T. Miura, Y. Funakoshi, M. Morimoto, T. Biyajima, M. Murakami, J. Am. Chem. Soc. 2012, 134, 17440.