Iron-catalyzed indirect hydration of alkynes in presence of methanesulfonic acid

Tetrahedron Letters

Volumn 54, Issue 33, 2013, Pages 4414-4417

  Park, Jungmin ^a   Yeon, Jihee ^a   Lee, Phil Ho ^a   Lee, Kooyeon ^a  

^a Kangwon National University   (South Korea)

Author keywords

Alkynes; Catalysis; Hydration; Iron; Ketones

Indexed keywords

ALKYNE DERIVATIVE; MESYLIC ACID; SULFONATED IMMUNOGLOBULIN; UNCLASSIFIED DRUG; VINYL SULFONATE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDRATION;

EID: 84880038665     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.06.015     Document Type: Article

References (37)

1. For review articles of hydration of alkynes, see: L. Hintermann, and A. Labonne Synthesis 2007 1121
2. F. Alonso, I.P. Beletskaya, and M. Yus Chem. Rev. 104 2004 3079
3. A. Corma, A. Leyva-Pérez, and M.J. Sabater Chem. Rev. 111 2011 1657
4. B.M. Trost Science 254 1991 1471
5. B.M. Trost Angew. Chem., Int. Ed. Engl. 34 1995 259
6. B. Neumann, and H. Schneider Angew. Chem. 33 1920 189
7. W.L. Budde, and R.E. Dessey J. Am. Chem. Soc. 85 1963 3964
8. V. Janout, and S.L. Regen J. Org. Chem. 47 1982 3331
9. M. Nishizawa, M. Skwarczynski, H. Imagawa, and T. Sugihara Chem. Lett. 2002 12
10. Y. Fukuda, and K. Utimoto J. Org. Chem. 56 1991 3729
11. J.H. Teles, S. Brode, and M. Chabanas Angew. Chem., Int. Ed. 37 1998 1415
12. E. Mizushima, K. Sato, T. Hayashi, and M. Tanaka Angew. Chem., Int. Ed. 41 2002 4563
13. R. Casado, M. Contel, M. Laguna, P. Romero, and S. Sanz J. Am. Chem. Soc. 125 2003 11925
14. P. Roembke, H. Schmidbaur, S. Cronje, and H. Raubenheimer J. Mol. Catal. A: Chem. 212 2004 35
15. A. Vasudevan, and M.K. Verzal Synlett 2004 631
16. N. Marion, R.S. Ramón, and S.P. Nolan J. Am. Chem. Soc. 131 2009 448
17. A.S.K. Hashmi, T. Hengst, C. Lothschütz, and F. Rominger Adv. Synth. Catal. 352 2010 1315
18. J. Halpern, B.R. James, and A.L.W. Kemp J. Am. Chem. Soc. 83 1961 4097
19. M.M. Taqui Khan, S.B. Halligudi, and S. Shukla J. Mol. Catal. 58 1990 299
20. M. Tokunaga, and Y. Wakatsuki Angew. Chem., Int. Ed. 37 1998 2867
21. D.B. Grotjahn, C.D. Incarnito, and A.L. Rheingold Angew. Chem., Int. Ed. 40 2001 3884
22. F. Chevallier, and B. Breit Angew. Chem., Int. Ed. 45 2006 1599
23. A. Labonne, T. Kribber, and L. Hintermann Org. Lett. 8 2006 5853
24. B.R. James, and G.L. Rempel J. Am. Chem. Soc. 91 1969 863
25. J. Blum, H. Huminer, and H. Alper J. Mol. Catal. 75 1992 153
26. J. Hartman, W.C. Hiscox, and P.W. Jennings J. Org. Chem. 58 1993 7613
27. W. Baidossi, M. Lahav, and J. Blum J. Org. Chem. 62 1997 669
28. D.W. Lucey, and J.D. Atwoood Organometallics 21 2002 2481
29. For osmium: W.D. Harman, J.C. Dobson, and H. Taube J. Am. Chem. Soc. 111 1989 3062
30. For iridium: H. Kanemitsu, K. Uehara, S. Fukuzumi, and S. Ogo J. Am. Chem. Soc. 130 2008 17141
31. S. Ogo, K. Uehara, T. Abura, Y. Watanabe, and S. Fukuzumi J. Am. Chem. Soc. 126 2004 16520
32. T. Hirabayashi, Y. Okimoto, A. Saito, M. Morita, S. Sakaguchi, and Y. Ishii Tetrahedron 62 2006 2231
33. For palladium: K. Imi, K. Imai, and K. Utimoto Tetrahedron Lett. 28 1987 3127
34. For iron: J.P. Damiano, and M. Pastel J. Organomet. Chem. 522 1996 303
35. X.-F. Wu, D. Bezier, and C. Darcel Adv. Synth. Catal. 351 2009 367
36. J.R. Cabrero-Antonio, A. Leyva-Pérez, and A. Corma Chem. Eur. J. 18 2012 11107
37. G.L. Bras, O. Provot, J.-F. Peyrat, M. Alami, and J.-D. Brion Tetrahedron Lett. 47 2006 5497