The search for new hydrogenation catalyst motifs based on N-heterocyclic carbene ligands

Inorganica Chimica Acta

Volumn 359, Issue 9, 2006, Pages 2786-2797

  Vazquez Serrano, Leslie D ^a   Owens, Bridget T ^a   Buriak, Jillian M ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Catalysis; Crabtree's catalyst; Dimer; Hydride; Hydrogenation; Iridium; N Heterocyclic carbenes; Non coordinating anion; Sterically hindered alkenes

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; DIMERS; HYDRIDES; HYDROGENATION; IRIDIUM; IRIDIUM COMPOUNDS; OLEFINS; PHOSPHORUS COMPOUNDS;

2 ,3-DIMETHYL-2-BUTENE; CATALYST RESTING STATE; CATALYTIC CONDITIONS; CATALYTICALLY ACTIVE SPECIES; COORDINATING ANIONS; HYDROGENATION CATALYST; N-HETEROCYCLIC CARBENE LIGANDS; N-HETEROCYCLIC CARBENES;

LIGANDS;

EID: 33646522920     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2005.10.049     Document Type: Article

References (67)

1. Rylander P.N. Hydrogenation Methods (1985), Academic Press, New York
2. Trost B.M. Science 254 (1991) 1471
3. Trost B.M. Angew. Chem., Int. Ed. Engl. 34 (1995) 259
4. Bläser H.-U., and Studer M. Appl. Catal. A: Gen. 189 (1999) 191
5. Trost B.M. Pure Appl. Chem. 66 (1994) 2007
6. Young J.F., Osborn J.A., Jardine F.H., and Wilkinson G.J. J. Chem. Soc., Chem. Commun. (1965) 131
7. Osborn J.A., Jardine F.H., Young J.F., and Wilkinson G.J. J. Chem. Soc. A (1966) 1711
8. Schrock R.R., and Osborn J.A. J. Am. Chem. Soc. 98 (1976) 2134
9. Schrock R.R., and Osborn J.A. J. Am. Chem. Soc. 98 (1976) 2143
10. Schrock R.R., and Osborn J.A. J. Am. Chem. Soc. 98 (1976) 4450
11. Crabtree R.H., Felkin H., and Morris G.E. J. Organomet. Chem. 141 (1977) 205
12. Crabtree R.H. Acc. Chem. Rev. 12 (1979) 331
13. Arduengo A.J., Rasika Dias H.V., Harlow R.L., and Kline M. J. Am. Chem. Soc. 114 (1992) 5530
14. Tafipolsky M., Scherer W., Öfele K., Artus G., Pedersen B., Herrmann W.A., and McGrady G.S. J. Am. Chem. Soc. 124 (2002) 5865
15. Arduengo A.J., Goerlich J.R., and Marshall W.J. J. Am. Chem. Soc. 117 (1995) 11027
16. Bourissou D., Guerret O., Gabbaï F.P., and Bertrand G. Chem. Rev. 100 (2000) 39
17. Lee H.M., Jiang T., Stevens E.D., and Nolan S.P. Organometallics 20 (2001) 1255
18. Perry M.C., and Burgess K. Tetrahedron: Asymmetry 14 (2003) 951
19. Scott N.M., Dorta R., Stevens E.D., Correa A., Cavallo L., and Nolan S.P. J. Am. Chem. Soc. 127 (2005) 3516
20. Scott N.M., and Nolan S.P. Eur. J. Inorg. Chem. (2005) 1815
21. Tolman C.A. Chem. Rev. 77 (1977) 313
22. Crudden C.M., Sateesh M., and Lewis R. J. Am. Chem. Soc. 127 (2005) 10045
23. Kim J.H., Kim J.W., Shokouhimehr M., and Lee Y.S. J. Org. Chem. 70 (2005) 6714
24. Peris E., and Crabtree R.H. Coord. Chem. Rev. 248 (2004) 2239
25. Albrecht M., Miecznikowski J.R., Samuel A., Faller J.W., and Crabtree R.H. Organometallics 21 (2002) 3596
26. Zarka M.T., Bortenschlager M., Wurst K., Nuyken O., and Weberskirch R. Organometallics 23 (2004) 4817
27. Mas-Marzá E., Poyatos M., Sanaú M., and Peris E. Inorg. Chem. 43 (2004) 2213
28. Maifeld S.V., Tran M.N., and Lee D. Tetrahedron Lett. 46 (2005) 105
29. Jafarpour L., and Nolan S.P. Organometallics 19 (2000) 2055
30. Grubbs R.H. Tetrahedron 60 (2004) 7117
31. Köcher C., and Herrmann W.A. J. Organomet. Chem. 532 (1997) 261
32. For review of some of the application of NHC's see. Herrmann W.A. Angew. Chem., Int. Ed. 41 (2002) 1290
33. Herrmann W.A., and Köcher C. Angew. Chem., Int. Ed. Engl. 36 (1997) 2162
34. Grasa G.A., Moore Z., Martin K.L., Stevens E.D., Nolan S.P., Paquet V., and Lebel H. J. Organomet. Chem. 658 (2002) 126
35. Powell M.T., Hou D.-R., Perry M.C., Cui X., and Burgess K. J. Am. Chem. Soc. 123 (2001) 8878
36. Cui X., Ogle J.W., and Burgess K. Chem. Commun. (2005) 672
37. Perry M.C., Cui X., Powell M.T., Hou D.-R., Reibenspies J.H., and Burgess K. J. Am. Chem. Soc. 125 (2003) 113
38. Cui X., and Burgess K. J. Am. Chem. Soc. 125 (2003) 14212
39. Blankenstein J., and Pfaltz A. Angew. Chem., Int. Ed. 40 (2001) 4445
40. Menges F., and Pfaltz A. Adv. Synth. Catal. 344 (2002) 40
41. Vazquez-Serrano L.D., Owens B.T., and Buriak J.M. Chem. Commun. (2002) 2518
42. Chatt J., and Venanzi L.M. J. Chem. Soc. (1957) 4735
43. Johnson W.S., and Schneider W.P. Org. Synth. Coll. 4 (1963) 132
44. Buriak J.M., Klein J.C., Herrigton D., and Osborn J.A. Chem. Eur. J. 6 (2000) 139
45. Herrmann W.A., Köcher C., Gooßen L.J., and Artus G.R.J. Chem. Eur. J. 2 (1996) 1627
46. A.J. Arduengo III, Preparation of 1,3-disubstituted Imidazolium Salts, U.S. Patent 5,077,414, 1991.
47. Buschmann W.E., and Miller J.S. Chem. Eur. J. 4 (1998) 1731
48. Brookhart M., Grant B., and Volpe Jr. A.F. Organometallics 11 (1992) 3920
49. Zuccaccia C., Bellachioma G., Cardaci G., and Macchioni A. J. Am. Chem. Soc. 123 (2001) 11020
50. Saba S., Brescia A.M., and Kaloustian M.K. Tetrahedron Lett. 32 38 (1991) 5031
51. Herrmann W.A., Elison M., Fischer J., Köcher C., and Artus G.R.J. Chem. Eur. J. 2 (1996) 772
52. Scholl M., Ding S., Lee C.W., and Grubbs R.H. Org. Lett. 1 (1999) 953
53. Trnka T.M., and Grubbs R.H. Acc. Chem. Res. 34 (2001) 18 and references within
54. Herrmann W.A., Reisinger C.-P., and Spiegler M. J. Organomet. Chem. 557 (1998) 93
55. Zhang C., Huang J., Trudell M.L., and Nolan S.P. J. Org. Chem. 64 (1999) 3804
56. Stauffer S.R., Lee S., Stambuli J.P., Hauck S.I., and Hartwig J.F. Org. Lett. 2 (2000) 1423
57. Lee S., and Hartwig J.F. J. Org. Chem. 66 (2001) 3402
58. Lee H.M., Jiang T., Stevens E.D., and Nolan S.P. Organometallics 20 (2001) 1255
59. Lightfoot A., Schnider P., and Pfaltz A. Angew. Chem., Int. Ed. Engl. 37 (1998) 2897
60. Drago D., Pregosin P.S., and Pfaltz A. Chem. Commun. (2002) 286
61. Martínez-Viviente E., and Pregosin P.S. Inorg. Chem. 42 (2003) 2209
62. Pfaltz A., Blankenstein J., Hilgraf R., Hörmann E., McIntyre S., Menges F., Schönleber M., Smidt S.P., Wüstenberg B., and Zimmermann N. Adv. Synth. Catal. 345 (2003) 33
63. Helmchen G., and Pfaltz A. Acc. Chem. Res. 33 (2000) 336
64. Chan Y.N.C., and Osborn J.A. J. Am. Chem. Soc. 112 (1990) 9400
65. Brandt P., Hedberg C., and Andersson P.G. Chem. Eur. J. (2003) 339
66. Fryzuk M.D., Piers W.E., Einstein F.W.B., and Jones T. Can. J. Chem. 67 (1989) 883
67. Fryzuk M.D. Can. J. Chem. 61 (1983) 1347