Iridium-catalyzed isomerization of primary allylic alcohols under mild reaction conditions

Tetrahedron Letters

Volumn 50, Issue 28, 2009, Pages 4141-4144

  Mantilli, Luca ^a   Mazet, Clément ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Allylic alcohols; Iridium; Isomerization; P,N Ligands

Indexed keywords

ALCOHOL; IRIDIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HYDROGENATION; ISOMERIZATION; ROOM TEMPERATURE; SYNTHESIS;

EID: 66049147273     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.04.130     Document Type: Article

References (42)

1. For recent reviews, see:. Van der Drift R.C., Bouwman E., and Drent E. J. Organomet. Chem. 650 (2002) 1-24
2. Uma R., Crévisy C., and Grée R. Chem. Rev. 103 (2003) 27-52
3. Cadierno V., Crochet P., and Gimeno J. Synlett (2008) 1105-1124
4. For relevant examples, see:. Bergens S., and Bosnich B. J. Am. Chem. Soc. 113 (1991) 958-967
5. Tanaka K., Qiao S., Tobisu M., Lo M.M.-C., and Fu G.C. J. Am. Chem. Soc. 122 (2000) 9870-9871
6. Uma R., Davies M.K., Crévisy C., and Grée R. Eur. J. Org. Chem. (2001) 3141-3146
7. Martin-Matute B., Bogár K., Edin M., Kaynak F.B., and Bäckvall J.E. Chem. Eur. J. 11 (2005) 5832-5842
8. Cadierno V., García-Garrido S.E., Gimeno J., Varela Álvarez A., and Sordo J.A. J. Am. Chem. Soc. 128 (2006) 1360-1370
9. Reetz M.T., and Hougchao G. Synlett (2006) 2127-2129
10. For mechanistic studies, see:. Trost B.M., and Kuliawec R.J. J. Am. Chem. Soc. 115 (1993) 2027-2036
11. McGrath, D. V.; Grubbs, R. H. Organometallics 1994, 13, 224-235
12. Tanaka K., and Fu G.C. J. Org. Chem. 66 (2001) 8177-8186
13. Schrock R.R., and Osborn J.A. J. Am. Chem. Soc. 98 (1976) 2134-2143
14. Chin C.S., Shin J.H., and Kim C. J. Organomet. Chem. 356 (1988) 381-388
15. Sun Y., Landau R.N., Wang J., LeBlond C., and Blackmond D.G. J. Am. Chem. Soc. 118 (1996) 1348-1353
16. Baudry D., Ephritikhine M., and Felkin H. Nouv. J. Chem. 2 (1978) 355-356
17. Crabtree R.H. Acc. Chem. Res. 12 (1979) 331-337
18. Stork G., and Kahne D. J. Am. Chem. Soc. 105 (1983) 1072-1073
19. Crabtree R.H., and Davis M.W. Organometallics 2 (1983) 681-682
20. Krel M., Lallemand J.-Y., and Guillou C. Synlett (2005) 2043-2046
21. Kavanagh Y., Chaney C.M., Muldoon J., and Evans P. J. Org. Chem. 73 (2008) 8601-8604
22. Fehr C., and Farris I. Angew. Chem. 118 (2006) 7058-7061
23. Angew. Chem. Int. Ed. 45 (2006) 6904-6907
24. Chin C.S., Park J., Kim C., Lee S.Y., Shin J.H., and Kim J.B. Catal. Lett. 1 (1988) 203-205
25. Chin C.S., and Lee B. J. Chem. Soc., Dalton Trans. (1991) 1323-1327
26. Lu X., Lin Y., and Ma D. Pure Appl. Chem. 60 (1988) 1299-1306
27. Brookhart M., Grant B., and Volpe A.F. Organometallics 11 (1992) 3920-3922
28. Smidt S.P., Zimmermann N., Studer M., and Pfaltz A. Chem. Eur. J. 10 (2004) 4685-4693
29. Vazquez-Serano L.D., Owens B.T., and Buriak J.M. Inorg. Chim. Acta 359 (2006) 2786-2797
30. Nama D., Butti P., and Pregosin P.S. Organometallics 26 (2007) 4942-4954
31. Wüstenberg B., and Pfaltz A. Adv. Synth. Catal. 350 (2008) 174-178
32. Chodosh D.F., Crabtree R.H., Felkin H., and Morris G.E. J. Organomet. Chem. 161 (1978) C67-C70
33. Wang H., Casalnuovo A.L., Johnson B.J., Mueting A., and Pignolet L.H. Inorg. Chem. 27 (1988) 325-331
34. Smidt S.P., Pfaltz A., Martinez-Viviente E., Pregosin P.S., and Albinati A. Organometallics 22 (2003) 1000-1009
35. Xu Y., Celik M.A., Thompson A.L., Cai H., Yurtsever M., Odell B., Green J.C., Mingos D.M.P., and Brown J.M. Angew. Chem. 121 (2009) 590-593 Angew. Chem. Int. Ed. 2009, 48, 582-585
36. See Supplementary data.
37. If the hydrogen atmosphere is maintained, the saturated alcohol is formed preferentially. See Supplementary data.
38. For recent reviews:. Cui X., and Burgess K. Chem. Rev. 105 (2005) 3272-3296
39. Källström K., Munslow I., and Andersson P.G. Chem. Eur. J. 12 (2006) 3194-3200
40. Roseblade S.J., and Pfaltz A. Acc. Chem. Res. 40 (2007) 1402-1411
41. Crabtree R.H., Demou P.C., Eden D., Mihelic J., Parnell C.A., Quirk J.M., and Morris G.E. J. Am. Chem. Soc. 104 (1982) 6994-7001
42. For identification of iridium-dihydride intermediate A, see Supplementary data.