Exploring the reactivity of 1,5-disubstituted sulfonyl-triazoles: Thermolysis and Rh(II)-catalyzed synthesis of α-sulfonyl nitriles This article is dedicated to Professor Paul Wender for both his creative contributions to synthetic organic chemistry and untiring mentorship

Tetrahedron

Volumn 69, Issue 36, 2013, Pages 7840-7846

  Meza Aviña, Maria Elena ^a   Patel, Mudita Kishor ^a   Croatt, Mitchell P ^a  

^a UNIVERSITY OF NORTH CAROLINA AT GREENSBORO   (United States)

Author keywords

Carbenes; Nitriles; Rhodium; Thermolysis; Triazoles

Indexed keywords

BRONSTED ACID; CARBENOID; LEWIS ACID; NITRILE; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; MELTING POINT; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PYROLYSIS; SYNTHESIS;

EID: 84880923114     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.05.048     Document Type: Article

References (29)

1. For a set of reviews in this area, see the themed issue: Chem. Soc. Rev. 39 2010 1221 1408
2. G.A. Patani, and E.J. LaVoie Chem. Rev. 96 1996 3147 3176
3. K. Odlo, J. Fournier-Dit-Chabert, S. Ducki, O.A.B.S.M. Gani, I. Sylte, and T.V. Hansen Bioorg. Med. Chem. 18 2010 6874 6885
4. K. Odlo, J. Hentzen, J.F. dit Chabert, S. Ducki, O.A.B.S.M. Gani, I. Sylte, M. Skrede, V.A. Flørenes, and T.V. Hansen Bioorg. Med. Chem. 16 2008 4829 4838
5. M.E. Meza-Aviña, M.K. Patel, C.B. Lee, T.J. Dietz, and M.P. Croatt Org. Lett. 13 2011 2984 2987
6. I.F.D. Hyatt, and M.P. Croatt Angew. Chem; Int. Ed. 51 2012 7511 7514
7. I.F.D. Hyatt, M.E. Meza-Aviña, and M.P. Croatt Synlett 2012 2869 2874
8. J.H. Boyer, C.H. Mack, N. Goebel, and L.R. Morgan J. Org. Chem. 23 1958 1051 1053
9. E. Robson, J.M. Tedder, and B. Webster J. Chem. Soc. 1963 1863 1865
10. R. Helwig, and M. Hanack Chem. Ber. 118 1985 1008 1021
11. R. Huisgen, R. Knorr, L. Möbius, and G. Szeimies Chem. Ber. 98 1965 4014 4021
12. E.J. Yoo, M. Ahlquist, S.H. Kim, I. Bae, V.V. Fokin, K.B. Sharpless, and S. Chang Angew. Chem; Int. Ed. 46 2007 1730 1733
13. F. Wang, H. Fu, Y. Jiang, and Y. Zhao Adv. Synth. Catal. 350 2008 1830 1834
14. R.E. Harmon, F. Stanley, S.K. Gupta, and J. Johnson J. Org. Chem. 35 1970 3444 3448
15. T. Horneff, S. Chuprakov, N. Chernyak, V. Gevorgyan, and V.V. Fokin J. Am. Chem. Soc. 130 2008 14972 14974
16. S. Chuprakov, S.W. Kwok, L. Zhang, L. Lercher, and V.V. Fokin J. Am. Chem. Soc. 131 2009 18034 18035
17. S. Chuprakov, J.A. Malik, M. Zibinsky, and V.V. Fokin J. Am. Chem. Soc. 133 2011 10352 10355
18. B. Chattopadhyay, and V. Gevorgyan Org. Lett. 13 2011 3746 3749
19. M. Zibinsky, and V.V. Fokin Angew. Chem; Int. Ed. 52 2013 1507 1510
20. A.V. Gulevich, and V. Gevorgyan Angew. Chem; Int. Ed. 52 2013 1371 1373
21. N. Selander, B.T. Worrell, and V.V. Fokin Angew. Chem; Int. Ed. 51 2012 13054 13057
22. T. Miura, Y. Funakoshi, M. Morimoto, T. Biyajima, and M. Murakami J. Am. Chem. Soc. 134 2012 17440 17443
23. N. Selander, B.T. Worrell, S. Chuprakov, S. Velaparthi, and V.V. Fokin J. Am. Chem. Soc. 134 2012 14670 14673
24. T.L. Gilchrist, G.E. Gymer, and C.W. Rees J. Chem. Soc. D, Chem. Commun. 1971 1519 1520
25. T.L. Gilchrist, G.E. Gymer, and C.W. Rees J. Chem. Soc; Perkin Trans. 1 1973 555 561
26. I. Bae, H. Han, and S. Chang J. Am. Chem. Soc. 127 2005 2038 2039
27. H. Zhao, and E.R. Biehl Synth. Commun. 25 1995 4063 4069
28. M.B. Cid, J. López-Cantarero, S. Duce, and J.L.G. Ruano J. Org. Chem. 74 2008 431 434
29. M.C. Pirrung The Synthetic Organic Chemist's Companion 2007 John Wiley & Sons Hoboken, NJ 171 172