N-Heterocyclic carbene-rhodium complexes as catalysts for hydroformylation and related reactions

Coordination Chemistry Reviews

Volumn 255, Issue 3-4, 2011, Pages 473-483

  Gil, W ^a   Trzeciak, A M ^a  

^a UNIVERSITY OF WROC AW   (Poland)

Author keywords

Hydroformylation; N heterocyclic carbene; Rhodium catalyst; Supported Rh carbene complex

Indexed keywords

EID: 78649905585     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2010.11.005     Document Type: Review

References (104)

1. Praetorius J.M., Crudden C.M. Dalton Trans. 2008, 4079.
2. Diez-Gonzalez S., Marion N., Nolan S.P. Chem. Rev. 2009, 109:3612.
3. Veige A.S. Polyhedron 2008, 27:3177.
4. Frohning C.D., Kohlpaitner C.W. Applied Homogenous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Two Volumes 1996, vol. 1:27. VCH Weinheim.
5. Cornils B. New Syntheses with Carbon Monoxide 1980, Springer, Berlin. J. Falbe (Ed.).
6. Rhodium Catalysed Hydroformylation 2000, Kluwer Academic Publisher, Dordrecht. P.W.N.M. van Leeuven, C. Claver (Eds.).
7. Thatchenko I. Comprehensive Organometallic Chemistry 1982, vol. 8:101. Pergamon, Oxford.
8. Parshall W.G. Homogenous Catalysis: The Application and Chemistry of Catalysis by soluble Transition Metal Complexes 1980, Wiley, New York.
9. Beller M., Cornils B., Frohning C.D., Kohlpaintner C.W. J. Mol. Catal. A: Chem. 1995, 104:17.
10. Evans D., Osborn J.A., Wilkinson G. J. Chem. Soc. A 1968, 3133.
11. Evans D., Yagupsky G., Wilkinson G. J. Chem. Soc. A 1968, 2660.
12. Brown C.K., Wilkinson G. J. Chem. Soc. A 1970, 2753.
13. Trzeciak A.M., Ziółkowski J.J. Coord. Chem. Rev. 1999, 190-192:883.
14. van der Veen L.A., Kamer P.C.J., van Leeuven P.W.N.M. Organometallics 1999, 18:4765.
15. Bronger R.P.J., Silva S.M., Kamer P.C.J., van P.W.N.M., Leeuven Dalton Trans. 2004, 1390.
16. Casey C.P., Paulsen E.L., Beuttenmueller E.W., Proft B.R., Petrovich L.M., Matter B.A., Powell D.R. J. Am. Chem. Soc. 1997, 118:11817.
17. Trzeciak A.M., Głowiak T., Grzybek R., Ziółkowski J.J. J. Chem. Soc. Dalton Trans. 1997, 1831.
18. Crudden C.M., Allen D.P. Coord. Chem. Rev. 2004, 248:2247.
19. Herrmann W.A. Angew. Chem. Int. Ed. 2002, 41:1290.
20. N-heterocyclic Carbenes in Synthesis 2006, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. S.P. Nolan (Ed.).
21. N-Heterocyclic carbenes in transition metal catalysis. Topics in Organometallic Chemistry 2007, Springer-Verlag, Berlin/Heidelberg. F. Glorius (Ed.).
22. Corberan R., Mas-Marza E., Peris E. Eur. J. Chem. 2009, 1700.
23. Tolman C.A. Chem. Rev. 1977, 77:313.
24. Heck F.R., Breslow D.S. J. Am. Chem. Soc. 1961, 83:4023.
25. Casey C.P., Petrovich L.M. J. Am. Chem. Soc. 1995, 117:6007.
26. Bronger R.P.J., Kamer P.C.J., van Leeuven P.W.N.M. Organometallics 2003, 22:5358.
27. Sparta M., Borve K.J., Jensen V.R. J. Am. Chem. Soc. 2007, 129:8487.
28. Kiss G., Mozeleski J.E., Nadler C.K., Van Driessche E., De C., Roover J. Mol. Catal. A: Chem. 1999, 138:135.
29. van der Slot S.C., Kamer P.C.J., van Leeuwen P.W.N.M., Iggo A.J., Heaton B.T. Organometallics 2001, 20:430.
30. Nozaki K., Matsuo T., Shibahara F., Hiyama T. Organometallics 2003, 22:594.
31. Kuil M., Solmer T., van Leeuwen P.W.N.M., Reek H.N.J. J. Am. Chem. Soc. 2006, 128:11344.
32. van Leeuwen P.W.N.M. Homogeneous Catalysis, Understanding the Art 2004, Kluwer, Dortrecht, (Chapter 8).
33. Trzeciak A.M., Mieczyńska E., Ziółkowski J.J. Top. Catal. 2000, 10/11:461.
34. Trzeciak A.M., Ziółkowski J.J., Choukroun R. J. Organomet. Chem. 1996, 525:145.
35. Pruett R.L., Smith J.A. J. Org. Chem. 1969, 34:327.
36. R.L. Pruett, J.A. Smith, W.V. Charleston, US Patent 3527809, Union Carbide Corporation (1970).
37. Pruett R.L. Adv. Organomet. Chem. 1979, 17:1.
38. Trzeciak A.M., Ziółkowski J.J. J. Mol. Catal. 1988, 48:319.
39. Trzeciak A.M., Ziółkowski J.J. J. Organomet. Chem. 1994, 464:107.
40. Trzeciak A.M., Wolszczak E., Ziółkowski J.J. New J. Chem. 1996, 20:365.
41. van Leeuven P.W.N.M., Roobeek C.F. J. Organomet. Chem. 1983, 258:343.
42. Poelsma S.N., Maitlis P.M. J. Organomet. Chem. 1993, 451:C15.
43. N. Yoshinura, Y. Tokito, European Patent 223103 (1987) (to Kuraray).
44. Köcher C., Herrmann W.A. J. Organomet. Chem. 1997, 532:261.
45. Tukov A.A., Normand A.T., Nechaev M.S. Dalton Trans. 2009, 7015.
46. Srebro M., Michalak A. Inorg. Chem. 2009, 48:5361.
47. Jongsma T., Challa G., van Leeuven P.W.N.M. J. Organomet. Chem. 1991, 421:121.
48. E. Billig, A.G. Abatjoglou, R.D. Bryant, U.S. Patent 4 668 651; European Patent Appl. 213 639, 1987 (to Union Carbide) Chem. Abstr. 107 (1987) 7392.
49. E. Billig, A.G. Abatjoglou, D.R. Bryant, R.E. Murray, J.M. Maher, U.S. Patent 4 599 206 (to Union Carbide) Chem. Abstr. 109 (1988) 233177.
50. Casey C.P., Whiteker G.T., Malville M.G., Petrovich L.M., Garney J.A., Powell D.R. J. Am. Chem. Soc. 1992, 114:5535.
51. Kranenburg M., van der Burgt Y.E.M., Kamer P.C.J., van P.W.N.M., Leeuwen Organometallics 1995, 14:3081.
52. Hillier A.C., Sommer W.J., Yong B.S., Petersen J.L., Cavallo L., Nolan S.P. Organometallics 2003, 22:4322.
53. Poyatos M., Uriz P., Mata J.A., Claver C., Fernandez E., Peris E. Organometallics 2003, 22:440.
54. Chen A.C., Ren L., Decken A., Crudden C.M. Organometallics 2000, 19:3459.
55. Zarka M.T., Bortenschlager M., Wurst K., Nuyken O., Weberskirch R. Organometallics 2004, 23:4817.
56. Dastgir S., Coleman K.S., Cowley A.R., Green M.L.H. Organometallics 2006, 25:300.
57. Bortenschlager M., Mayr M., Nuyken O., Buchmeiser M.R. J. Mol. Catal. A: Chem. 2005, 233:67.
58. Llewellyn S.A., Green M.L.H., Cowley A.R. Dalton Trans. 2006, 4164.
59. Praetorius J.M., Kotyk M.W., Webb J.D., Wang R.Y., Crudden C.M. Organometallics 2007, 26:1057.
60. Gual A., Godard C., Castillon S., Claver C. Tetrahedron: Asymmetry 2010, 27:1135.
61. Sakai N., Mano S., Nozaki K., Takaya H. J. Am. Chem. Soc. 1993, 115:7033.
62. Nozaki K., Sakai N., Nanno T., Higashijima T., Mano S., Horiuchi T., Takaya H. J. Am. Chem. Soc. 1997, 119:4413.
63. Gleich D., Herrmann W.A. Organometallics 1999, 18:4354.
64. Tanaka R., Nakano K., Nozaki K. J. Org. Chem. 2007, 72:8671.
65. Nozaki K., Ito Y., Shibahara F., Shirakawa E., Otha T., Takaya H., Hiyama T. J. Am. Chem. Soc. 1998, 120:4051.
66. Buisman H.J.G., Van der Veen A.L., de Lange J.G.W., Kamer P.C.J., van Leeuwen P.W.N.M., Vogt D. Organometallics 1997, 16:2929.
67. Axtell T.A., Klosin J., Abboud A.K. Organometallics 2006, 25:5003.
68. Axtell T.A., Colbey J.C., Klosin J., Whiteker T.G., Zanotti-Gerosa A., Abbout A.K. Angew. Chem. Int. Ed. 2005, 44:5834.
69. Lai R., Daran J.-C., Heumann A., Zaragori-Benedetti A., Rafi E. Inorg. Chem. Acta 2009, 362:4849.
70. Jeletic M.S., Jan M.T., Ghiviriga I., Abboud K.A., Veige A.S. Dalton Trans. 2009, 2764.
71. Song H., Lu L.-N., Zi G. J. Organomet. Chem. 2009, 694:1493.
72. Zinner S.C., Herrmann W.A., Kuhn F.E. J. Organomet. Chem. 2008, 693:1543.
73. W.A. Herrmann, J. Fischer, M. Elison, C. Ko{double acute}cher, DE 4447068 (1994) (to Hoechst).
74. Bortenschlager M., Schutz J., von Preysing D., Nuyken O., Weberskirch R. J. Organomet. Chem. 2005, 690:6233.
75. Dastgir S., Coleman K.S., Cowley A.R., Green M.L.H. Dalton Trans. 2009, 7203.
76. Gil W., Trzeciak A.M., Ziółkowski J.J. Organometallics 2008, 27:4131.
77. Neveling A., Julius G.R., Cronje S., Esterhuysen C., Raubenheimer H.G. Dalton Trans. 2005, 181.
78. Downing S.P., Pogorzelec P.J., Donopoulos A.A., Cole-Hamilton D.J. Eur. J. Inorg. Chem. 2009, 1816.
79. Gil W., Boczoń K., Trzeciak A.M., Ziółkowski J.J., Garcia-Verdugo E., Luis S.V., Sans V. J. Mol. Catal. A: Chem. 2009, 309:131.
80. Trzeciak A.M. J. Organomet. Chem. 1990, 390:105.
81. Trzeciak A.M., Głowiak T., Ziółkowski J.J. J. Organomet. Chem. 1998, 552:159.
82. Van der Veen L.A., Kamer P.C.J., van P.W.N.M., Leeuwen Organometallics 1999, 18:4765.
83. Solsona A., Suades J., Mathieu R. J. Organomet. Chem. 2003, 669:172.
84. van der Slot S.C., Duran J., Luten J., Kamer P.C.J., van P.W.N.M., Leeuwen Organometallics 2002, 21:3873.
85. van der Slot S.C., Kamer P.C.J., van Leeuwen P.W.N.M., Fraanje J., Goubitz K., Lutz M., Spek A.L. Organometallics 2000, 19:2504.
86. van der Slot S.C., Kamer P.C.J., van Leeuwen P.W.N.M., Iggo J.A., Heaton B.T. Organometallics 2001, 20:430.
87. Scholten J.D., Dupont J. Organometallics 2008, 27:4439.
88. Douglas S., Lowe J.P., Mahon M.F., Warren J.E., Whittlesey M.K. J. Organomet. Chem. 2005, 690:5027.
89. Yu X., Sun H., Patrick B.O., James B.R. Eur. J. Inorg. Chem. 2009, 1752.
90. Praetorius J.M., Wang R., Crudden C.M. Eur. J. Inorg. Chem. 2009, 1746.
91. Huang J., Stevens E.D., Nolan S.P. Organometallics 2000, 19:1194.
92. Herrmann W.A., Frey G.D., Herdtweck E., Steinbeck H. Adv. Synth. Catal. 2007, 349:1677.
93. Jong H., Patrick B.O., Fryzuk M.D. Can. J. Chem. Rev. Can. Chem. 2008, 86:803.
94. Dyson G., Frison J.-C., Whitwood A.C., Douthwaite R.E. Dalton Trans. 2009, 7141.
95. Grasa G.A., Moore Z., Martin K.L., Stevens E.D., Nolan S.P., Paquet V., Lebel H. J. Organomet. Chem. 2002, 658:126.
96. Allen D.P., Crudden C.M., Calhoun L.A., Wang R., Decken A. J. Organomet. Chem. 2005, 69:5736.
97. Meier N., Hahn F.E., Pape T., Siering C., Waldvogel S.R. Eur. J. Inorg. Chem. 2007, 1210.
98. Page M.J., Wagler J., Messerle B.A. Dalton Trans. 2009, 7029.
99. Messerle B.A., Page M.J., Turner P. Dalton Trans. 2006, 3927.
100. Binobaid A., Iglesias M., Beetstra D.J., Kariuki B., Dervisi A., Fallis I.A., Cavell K.J. Dalton Trans. 2009, 7099.
101. Arnanz A., Gonzalez-Arellano C., Juan A., Villaverde G., Corma A., Iglesias M., Sanchez F. Chem. Commun. 2010, 46:3001.
102. Bappert E., Helmchen G. Synth. Lett. 2004, 1789.
103. Baskakov D., Herrmann W.A., Herdtweck E., Hoffmann S.D. Organometallics 2007, 26:626.
104. Herrmann W.A., Baskakov D., Herdtweck E., Hoffmann S.D., Bunlaksananusorn T., Rampf F., Rodefeld L. Organometallics 2006, 25:2449.