Preparation, properties, and reactivity of carbonylrhodium(I) complexes of di(2-pyrazolylaryl)amido-pincer ligands

Journal of Organometallic Chemistry

Volumn 696, Issue 23, 2011, Pages 3623-3636

  Wanniarachchi, Sarath ^a   Liddle, Brendan J ^a   Lindeman, Sergey V ^a   Gardinier, James R ^a  

^a Marquette University   (United States)

Author keywords

Carbonylrhodium(I); Copper catalyzed amination; IR spectroscopy; NNN pincer ligands; Oxidative addition

Indexed keywords

ACETONE SOLUTION; ARYL SUBSTITUENTS; CARBONYLRHODIUM(I); CO DISSOCIATIONS; COUPLING REACTION; DETAILED KINETICS; ELECTRON-RICH; IODOETHANE; IODOMETHANE; NNN PINCER LIGANDS; OXIDATIVE ADDITIONS; PINCER LIGANDS; PYRAZOLYL; RELATIVE ORDER; RHODIUM COMPLEXES; ROOM TEMPERATURE; SECOND-ORDER RATE CONSTANTS; STRETCHING FREQUENCY; THREE ORDERS OF MAGNITUDE;

ACETONE; CATALYSIS; INFRARED SPECTROSCOPY; LIGANDS; METAL COMPLEXES; RATE CONSTANTS; RHODIUM; SCAFFOLDS; SUBSTITUTION REACTIONS;

RHODIUM COMPOUNDS;

EID: 80053913729     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2011.08.013     Document Type: Article

References (108)

1. C.J. Moulton, and B.L. Shaw J. Chem. Soc. Dalton Trans. 1976 1020 1024
2. D. Morales-Morales, and C. Jensen The Chemistry of Pincer Compounds 2007 Elsevier Amsterdam
3. G. van Koten, J.T.B.H. Jastrzebski, J.G. Noltes, A.L. Spek, and J.C. Schoone J. Organomet. Chem. 148 1978 233 245
4. G. van Koten, K. Timmer, J.G. Noltes, and A.L. Spek J. Chem. Soc. Chem. Commun. 1978 250 252
5. G. van Koten Pure Appl. Chem. 61 1989 1681 1694
6. A.A.H. van der Zeijden, G. van Koten, R. Luijk, K. Vrieze, C. Slob, H. Krabbendam, and A.L. Spek Inorg. Chem. 27 1988 1014 1019
7. A.A.H. van der Zeijden, G. van Koten, R.A. Nordemann, B. Kojić-Rodić, and A.L. Spek Organometallics 7 1988 1957 1966
8. A.A.H. van der Zeijden, G. van Koten, J.M. Ernsting, C.J. Elsevier, B. Krijnen, and C.H. Stam J. Chem. Soc. Dalton Trans. 1989 317 324
9. M. Albrecht, and M.M. Lindner Dalton Trans. 40 2011 Advanced Article, doi:10.1039/c1dt10339c
10. J. Choi, A.H.R. MacArthur, M. Brookhart, and A.S. Goldman Chem. Rev. 111 2011 1761 1779
11. N. Selander, and K.J. Szabó Chem. Rev. 111 2011 2048 2076
12. L.-C. Liang, J.-M. Lin, and C.-H. Hung Organometallics 22 2003 3007 3009
13. See also asymmetric derivatives: R.B. Lansing Jr., K.I. Goldberg, and R.A. Kemp Dalton Trans. 40 2011 Advanced Article, doi:10.1039/c1dt10265f
14. P. Surawatanawong, and O.V. Ozerov Organometallics 30 2011 2972 2980
15. M. Puri, S. Gatard, D.A. Smith, and O.V. Ozerov Organometallics 30 2011 2472 2485
16. S. Gatard, C.-H. Chen, B.M. Foxman, and O.V. Ozerov Organometallics 27 2008 6257 6267
17. S. Gatard, C. Guo, B.M. Foxman, and O.V. Ozerov Organometallics 26 2007 6066 6075
18. S. Gatard, R. elenligil-etin, C. Guo, B.M. Foxman, and O.V. Ozerov J. Am. Chem. Soc. 128 2006 2808 2809
19. A.M. Winter, K. Eichele, H.-G. Mack, S. Potuznik, H.A. Mayer, and W.C. Kaska J. Organomet. Chem. 682 2003 149 154
20. M. Feller, M.A. Iron, L.J.W. Shimon, Y. Diskin-Posner, G. Leitus, and D. Milstein J. Am. Chem. Soc. 130 2008 14374 14375
21. A.Y. Verat, H. Fan, M. Pink, Y.-S. Chen, and K.G. Caulton Chem. Eur. J. 14 2008 7680 7686
22. A.Y. Verat, M. Pink, H. Fan, J. Tomaszewski, and K.G. Caulton Organometallics 27 2008 166 168
23. W.-W. Xu, G.P. Rosini, M. Gupta, C.M. Jensen, W.C. Kaska, K. Krogh-Jespersen, and A.S. Goldman Chem. Commun. 1997 2273 2274
24. M. Gupta, C. Hagen, R.J. Flesher, W.C. Kaska, and C.M. Jensen Chem. Commun. 1996 2083-2084 and 2687
25. M. Montag, I. Efremenko, R. Cohen, L.J.W. Shimon, G. Leitus, Diskin- Y. Posner, Y. Ben-David, H. Salem, J.M.L. Martin, and D. Milstein Chem. Eur. J. 16 2010 328 (and references)
26. C.M. Frech, and D. Milstein J. Am. Chem. Soc. 128 2006 12434 12435
27. D.F. MacLean, R. McDonald, M.J. Ferguson, A.J. Caddell, and L. Turculet Chem. Commun. 2008 5146 5148
28. M. Delferro, M. Tegoni, V. Verdolino, D. Cauzzi, C. Graiff, and A. Tiripicchio Organometallics 28 2009 2062 2071
29. M. Doux, L. Ricard, P. Le Foch, and Y. Jean Organometallics 25 2006 1101 1111
30. M.E. El-Zaria, H. Arii, and H. Nakamura Inorg. Chem. 50 2011 4149 4161
31. T. Zweifel, J.-V. Naubron, and H. Grützmacher Angew. Chem. Int. Ed. 48 2009 559 563
32. T. Büttner, J. Geier, G. Frison, J. Harmer, C. Calle, A. Schweiger, H. Schönberg, and H. Grützmacher Science 307 2005 235 238
33. B. Wucher, M. Moser, S.A. Schumacher, F. Rominger, and D. Kunz Angew. Chem. Int. Ed. 48 2009 4417 4421
34. M. Moser, B. Wucher, D. Kunz, and F. Rominger Organometallics 26 2007 1024 1030
35. Ligand A, Chart 1, n = 1
36. S. Radi, S. Tighadouini, Y. Toubi, and M. Bacquet J. Hazard. Mater. 185 2011 494 503
37. H. Yang, Y. Tang, Z.-F. Shang, X.-L. Han, and Z.-H. Zhang Polyhedron 28 2009 3491 3498
38. W.L. Driessen, W.G.R. Wiesmeijer, M. Schipper-Zablotskaja, R.A.G. De Graaff, and J. Reedijk Inorg. Chim. Acta 162 1989 233 238
39. W.L. Driessen, R.A.G. De Graaff, J. Ochocki, and J. Reedijk Inorg. Chim. Acta 150 1988 41 45 Ligand A, Chart 1, n = 2
40. T.N. Sorrell, and M.R. Malachowski Inorg. Chem. 21 1983 1883 1887
41. S. Alves, A. Paulo, J.D.G. Correia, Â Domingos, and I. Santos J. Chem. Soc. Dalton Trans. 2002 4714 4719
42. S. Alves, A. Paulo, J.D.G. Correia, L. Gano, C.J. Smith, T.J. Hoffman, and I. Santos Bioconjug. Chem. 16 2005 438 449
43. Ligand B, Chart 1
44. W.I. Dzik, L.F. Arruga, M.A. Siegler, A.L. Spek, J.N.H. Reek, and B. de Bruin Organometallics 30 2011 1902 1913
45. W.I. Dzik, C. Creusen, R. de Gelder, T.P.J. Peters, J.M.M. Smits, and B. de Bruin Organometallics 29 2010 1629 1641
46. C. Tejel, M.P. del Río, M.A. Ciriano, E.J. Reijerse, F. Hartl, S. Záliŝ, D.G.H. Hetterscheid, N.T.I. Spithas, and B. de Bruin Chem. Eur. J. 15 2009 11878 11889
47. C. Tejel, M.P. del Río, M.A. Ciriano, M.P. del Río, F.J. van den Bruele, D.G.H. Hetterscheid, N.T.I. Spithas, and B. de Bruin J. Am. Chem. Soc. 130 2008 5844 5845
48. D.G.H. Hetterscheid, M. Klop, R.J.N.A.M. Kicken, J.M.M. Smits, E.J. Reijerse, and B. de Bruin Chem. Eur. J. 13 2007 3386 3405
49. Ligand C, Chart 1: F. Konrad, J.L. Fillol, H. Wadepohl, and L.H. Gade Inorg. Chem. 48 2009 8523 8532
50. Ligand D, Chart 1
51. J.L. Cryder, A.J. Killgore, C. Moore, J.A. Golen, A.L. Rheingold, and C.J.A. Daley Dalton Trans. 39 2010 10671 10677
52. B.K. Langlotz, H. Wadepohl, and L.H. Gade Angew. Chem. Int. Ed. 47 2008 4670 4674
53. Ligand E, Chart 1
54. M. Inoue, and M. Nakada Heterocycles 72 2007 133 138
55. M. Inoue, and M. Nakada Angew. Chem. Int. Ed. 45 2006 252 255
56. Ligand F, Chart 1
57. J.A. Gaunt, V.C. Gibson, A. Haynes, S.K. Spitzmesser, A.J.P. White, and D.J. Williams Organometallics 23 2004 1015 1023
58. For an alternative ligand preparation, see: A.M. Hollas, W. Gu, N. Bhuvanesh, and O.V. Ozerov Inorg. Chem. 50 2011 3673 3679
59. Ligand G, Chart 1: M.S. Mudadu, A.N. Singh, and R.P. Thummel J. Org. Chem. 73 2008 6513 6520
60. Ligand H, Chart 1
61. T. Inagaki, A. Ito, J.-I. Ito, and H. Nishiyama Angew. Chem. Int. Ed. 49 2010 9384 9387
62. H.;Liu, and D.-M. Du Eur. J. Org. Chem. 2010 2121 2131
63. Ligand I, Chart 1
64. D.S.C. Black, and N.E. Rothnie Tetrahedron Lett. 31 1978 28352838
65. D.S.C. Black, and N.E. Rothnie Aust. J. Chem. 36 1983 2395 2406
66. S.A. Cameron, and S. Brooker Inorg. Chem. 50 2011 3697 3699
67. Ligand J, Chart 1
68. P. Ren, O. Vechorkin, Z. Csok, I. Salihu, R. Scopelliti, and X. Hu Dalton Trans. 40 2011 Advance Article, doi:10.1039/c1dt10195a
69. J. Breitenfeld, O. Vechorkin, C. Corminboeuf, R. Scopelliti, and X. Hu Organometallics 29 2010 3686 3689
70. Z. Csok, O. Vechorkin, S.B. Harkins, R. Scopelliti, and X. Hu J. Am. Chem. Soc. 130 2008 8156 8157
71. Ligands K and L, Chart 1
72. J.C. Peters, S.B. Harkins, S.D. Brown, and M.W. Day Inorg. Chem. 40 2001 5083 5091
73. T.A. Betley, B.A. Qian, and J.C. Peters Inorg. Chem. 47 2008 11570 11582
74. Other rhodium complexes of NNN-pincers
75. J.H.H. Ho, D. St Clair Black, B.A. Messerle, J.K. Clegg, and P. Turner Organometallics 25 2006 5800 5810
76. M. Kooistra, D.G.H. Hetterscheid, E. Schwartz, Q. Knijnenburg, P.H.M. Budzelaar, and A.W. Gal Inorg. Chim. Acta 357 2004 2945 2952
77. S. Wanniarachchi, B.J. Liddle, J. Toussaint, S.V. Lindeman, B. Bennett, and J.R. Gardinier Dalton Trans. 40 2011 8776 8787
78. S. Wanniarachchi, B.J. Liddle, J. Toussaint, S.V. Lindeman, B. Bennett, and J.R. Gardinier Dalton Trans. 39 2010 3167 3169
79. M. Montag, L. Schwartsburd, R. Cohen, G. Leitus, Y. Ben-David, J.M.L. Martin, and D. Milstein Angew. Chem. Int. Ed. 46 2007 1901 1903
80. M.A.F. Hernandez-Gruel, J.J. Pérez-Torrente, M.A. Ciriano, and L.A. Oro Inorg. Synth. 34 2004 128
81. B.J. Liddle, R.M. Silva, T.J. Morin, F.P. Macedo, R. Shukla, S.V. Lindeman, and J.R. Gardinier J. Org. Chem. 72 2007 5637 5646
82. T.J. Morin, S.V. Lindeman, and J.R. Gardinier Eur. J. Inorg. Chem. 2009 104 110
83. SMART APEX2 Version 2.1-4, SAINT+Version 7.23a and SADABS Version 2004/1 2005 Bruker Analytical X-ray Systems, Inc. Madison, Wisconsin, USA
84. CrysAlisPro, Agilent Technologies, Version 1.171.34.46 (release 25-11-2010 CrysAlis171.NET), (compiled Nov 25 2010,17:55:46).
85. G.M. Sheldrick SHELXTL Version 6.12 2001 Bruker Anal. X-ray Systems, Inc. Madison Wisconsin, USA
86. SCALE3 ABSPACK - An Oxford Diffraction Program (1.0.4, gui:1.0.3) (C) 2005 Oxford Diffraction Ltd
87. H.-J. Cristau, P.P. Cellier, J.-F. Spindler, and M. Taillefer Eur. J. Org. Chem. 2004 695 709
88. M. Taillefer, N. Xia, and A. Ouali Angew. Chem. Int. Ed. 46 2007 934 936
89. H.-J. Christau, P.P. Cellier, J.-F. Spindler, and M. Taillefer Chem. Eur. J. 10 2004 5607 5622
90. See also, J.M. Lindley, I.M. McRobbie, O. Meth-Cohn, and H. Suschitzky J. Chem. Soc. Perkin Trans. 1 1980 982 994
91. J.C. Antilla, J.M. Baskin, T.E. Barder, and S.L. Buchwald J. Org. Chem. 69 2004 5578 5587
92. B.J. Liddle, and J.R. Gardinier J. Org. Chem. 72 2007 9794 9797
93. R. Mathieu, G. Esquius, N. Lugan, J. Pons, and J. Ros Eur. J. Inorg. Chem. 2001 2683 2688
94. A. Boixassa, J. Pons, J. Ros, R. Mathieu, and N. Lugan J. Organomet. Chem. 682 2003 233 239
95. J. García-Anton, R. Mathieu, N. Lugan, J.P. Picart, and J. Ros J. Organomet. Chem. 689 2004 1599 1602
96. J. Huang, C.M. Haar, S.P. Nolan, W.J. Marshall, and K.G. Moloy J. Am. Chem. Soc. 120 1998 7806 7815
97. C. Hansch, and A. Leo Substituent Constants for Correlation Analysis in Chemistry and Biology 1979 Wiley-Interscience New York
98. J.M. Wilson, G.J. Sunley, H. Adams, and A. Haynes J. Organomet. Chem. 690 2005 6089 6095
99. J. Rankin, A.C. Benyei, A.D. Poole, and D.J. Cole-Hamilton J. Chem. Soc. Dalton Trans. 1999 3771 3782
100. A.J. Hart-Davis, and W.A.G. Graham Inorg. Chem. 9 1970 2658 2663
101. J.P. Collmann, L.S. Hegedus, J.R. Norton, and R.G. Finke Principles and Applications of Organotransition Metal Chemisty second ed. 1987 University Science Books Mill Valley, CA
102. R.H. Crabtree The Organometallic Chemistry of the Transition Metals fifth ed. 2009 Wiley-Interscience New York (Chapter 6 and 12)
103. P.W.N.M. van Leeuwen Homogeneous Catalysis: Understanding the Art 2004 Kluwer Academic Publishers Dordrecht (Chapter 2 and 6)
104. J. Hartwig Organotransition Metal Chemsitry: From Bonding to Catalysis 2010 University Science Books Mill Valley, CA (Chapters 5-7)
105. P.R. Ellis, J.M. Pearson, A. Haynes, H. Adams, N.A. Bailey, and P.M. Maitlis Organometallics 13 1994 3215 3226 (and references)
106. R.J. Rubio, G.T.S. Andavan, E.B. Bauer, T.K. Hollis, J. Cho, F.S. Than, and B. Donnadieu J. Organomet. Chem. 690 2005 5353 5364
107. A. Haynes, P.M. Maitlis, I.A. Stanbridge, S. Haak, J.M. Pearson, H. Adams, and N.A. Bailey Inorg. Chim. Acta 357 2004 3027 3037
108. S. Fustero, M. Sánchez-Roselló, P. Barrio, and A. Simón-Fuentes Chem. Rev. 111 2011 ASAP, dx.doi:org/10.1021/cr2000459