CO2 insertion into metal-carbon bonds: A computational study of RhI pincer complexes

Chemistry - A European Journal

Volumn 17, Issue 37, 2011, Pages 10329-10338

  Ostapowicz, Thomas G ^a   Hölscher, Markus ^a   Leitner, Walter ^a,b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

carbon dioxide; density functional calculations; insertion; pincer ligands; rhodium

Indexed keywords

ACTIVATION BARRIERS; ALKYL-CHAIN; BOND-FORMING STEP; BUILDING BLOCKES; CARBON ATOMS; CATALYTIC CARBOXYLATION; CATALYTIC CYCLES; COMPUTATIONAL STUDIES; DENSITY-FUNCTIONAL CALCULATIONS; DONOR GROUPS; INSERTION; INSERTION REACTIONS; ORBITAL INTERACTION; PINCER COMPLEXES; PINCER LIGANDS; STERIC PROPERTIES; TRANSITION STATE;

CARBOXYLATION; COMPLEXATION; ELECTRONIC PROPERTIES; LIGANDS; RHODIUM;

CARBON DIOXIDE;

EID: 80052229514     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101463     Document Type: Article

References (106)

1. H. Arakawa, M. Aresta, J. N. Armor, M. A. Barteau, E. J. Beckman, A. T. Bell, J. E. Bercaw, C. Creutz, E. Dinjus, D. A. Dixon, K. Domen, D. L. DuBois, J. Eckert, E. Fujita, D. H. Gibson, W. A. Goddard, D. W. Goodman, J. Keller, G. J. Kubas, H. H. Kung, J. E. Lyons, L. E. Manzer, T. J. Marks, K. Morokuma, K. M. Nicholas, R. Periana, L. Que, J. Rostrup-Nielson, W. M. H. Sachtler, L. D. Schmidt, A. Sen, G. A. Somorjai, P. C. Stair, B. R. Stults, W. Tumas, Chem. Rev. 2001, 101, 953-996.
2. M. Peters, B. Köhler, W. Kuckshinrichs, W. Leitner, P. Markewitz, T. E. Müller, ChemSusChem, 2011, DOI:.
3. A. Behr, Chem. Ing. Tech. 1985, 57, 893-903
4. D. Walther, Coord. Chem. Rev. 1987, 79, 135-174
5. P. Braunstein, D. Matt, D. Nobel, Chem. Rev. 1988, 88, 747-764
6. W. Leitner, Angew. Chem. 1995, 107, 2391-2405
7. Angew. Chem. Int. Ed. Engl. 1995, 34, 2207-2221
8. W. Leitner, Coord. Chem. Rev. 1996, 153, 257-284
9. Y. Guari, S. Sabo-Etienne, B. Chaudret, Eur. J. Inorg. Chem. 1999, 1047-1055
10. C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639
11. M. Aresta, A. Dibenedetto, Catal. Today 2004, 98, 455-462
12. P. G. Jessop, F. Joó, C.-C. Tai, Coord. Chem. Rev. 2004, 248, 2425-2442
13. J. Louie, Curr. Org. Chem. 2005, 9, 605-623
14. T. Sakakura, J.-C. Choi, H. Yasuda, Chem. Rev. 2007, 107, 2365-2387
15. M. Aresta, A. Dibenedetto, Dalton Trans. 2007, 2975-2992
16. S. N. Riduan, Y. Zhang, Dalton Trans. 2010, 39, 3347-3357
17. M. Mikkelsen, M. JÃrgensen, F. C. Krebs, Energy Environ. Sci. 2010, 3, 43-81.
18. A. Behr, Carbon Dioxide Activation by Metal Complexes, VCH, Weinheim, 1988
19. W. Leitner, E. Dinjus, F. Ganer, in Aqueous-Phase Organometallic Catalysis: Concepts and Applications (Eds.:, B. Cornils, W. A. Herrmann,), Wiley-VCH, Weinheim, 1998, pp. 486-498
20. M. Aresta, in Activation of Small Molecules: Organometallic and Bioinorganic Perspective (Ed.:, W. B. Tolman,), VCH, Weinheim, 2006, Chapter 1.
21. F. R. Hartley, S. Patai, The Chemistry of Metal-Carbon Bonds, Vol. 3, Wiley, New York, 1985.
22. 2 insertions into Moi- and Wi-C bonds:, A. Galindo, A. Pastor, P. J. Pérez, E. Carmona, Organometallics 1993, 12, 4443-4451.
23. 2 insertions into Fei-C bonds:, S. D. Ittel, C. A. Tolman, A. D. English, J. P. Jesson, J. Am. Chem. Soc. 1978, 100, 7577-7585.
24. K. Osakada, R. Sato, T. Yamamoto, Organometallics 1994, 13, 4645-4647
25. S. Saito, S. Nakagawa, T. Koizumi, K. Hirayama, Y. Yamamoto, J. Org. Chem. 1999, 64, 3975-3978
26. M. Takimoto, M. Mori, J. Am. Chem. Soc. 2002, 124, 10008-10009
27. M. Aoki, M. Kaneko, S. Izumi, K. Ukai, N. Iwasawa, Chem. Commun. 2004, 2568-2569
28. C. M. Williams, J. B. Johnson, T. Rovis, J. Am. Chem. Soc. 2008, 130, 14936-14937
29. C. Bruckmeier, M. W. Lehenmeier, R. Reichardt, S. Vagin, B. Rieger, Organometallics 2010, 29, 2199-2202.
30. P. Braunstein, D. Matt, D. J. Nobel, J. Am. Chem. Soc. 1988, 110, 3207-3212
31. M. Aresta, E. Quaranta, I. Tommasi, New J. Chem. 1994, 18, 133-142
32. E. Dinjus, W. Leitner, Appl. Organomet. Chem. 1995, 9, 43-50
33. M. Shi, K. M. Nicholas, J. Am. Chem. Soc. 1997, 119, 5057-5058
34. S. Pitter, E. Dinjus, J. Mol. Catal. A: Chem. 1997, 125, 39-45
35. R. Johansson, M. Jarenmark, O. F. Wendt, Organometallics 2005, 24, 4500-4502
36. K. Ukai, M. Aoki, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2006, 128, 8706-8707
37. R. Johansson, O. F. Wendt, Dalton Trans. 2007, 488-492
38. C. S. Yeung, V. M. Dong, J. Am. Chem. Soc. 2008, 130, 7826-7827
39. J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2008, 130, 15254-15255
40. A. Correa, R. Martin, J. Am. Chem. Soc. 2009, 131, 15974-15975
41. J. Wu, J. C. Green, N. Hazari, D. P. Hruszkewycz, C. D. Incarvito, T. J. Schmeier, Organometallics 2010, 29, 6369-6376.
42. J. F. Hartwig, R. G. Bergman, R. A. Andersen, J. Am. Chem. Soc. 1991, 113, 6499-6508
43. O. R. Allen, S. J. Dalgarno, L. D. Field, P. Jensen, A. C. Willis, Organometallics 2009, 28, 2385-2390.
44. D. J. Darensbourg, G. Grötsch, P. Wiegreff, A. L. Rheingold, Inorg. Chem. 1987, 26, 3827-3830
45. H. Mizuno, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2011, 133, 1251-1253.
46. 2 insertions into Cui-C bonds
47. N. P. Mankad, T. G. Gray, D. S. Laitar, J. P. Sadighi, Organometallics 2004, 23, 1191-1193
48. L. Zhang, J. Cheng, T. Ohishi, Z. Hou, Angew. Chem. 2010, 122, 8852-8855
49. Angew. Chem. Int. Ed. 2010, 49, 8670-8673
50. I. I. F. Boogaerts, G. C. Fortman, M. R. L. Furst, C. S. J. Cazin, S. P. Nolan, Angew. Chem. 2010, 122, 8856-8859
51. Angew. Chem. Int. Ed. 2010, 49, 8674-8677.
52. 2 insertions into Aui-C bonds:, I. I. F. Boogaerts, S. P. Nolan, J. Am. Chem. Soc. 2010, 132, 8858-8859.
53. V. Branchadell, A. Dedieu, Inorg. Chem. 1987, 26, 3966-3968
54. G. Schubert, I. Pápai, J. Am. Chem. Soc. 2003, 125, 14847-14858.
55. A. Dedieu, C. Bo, F. Ingold, Chapter 4 in. Enzymatic and Model Carboxylation and Reduction Reactions for Carbon Dioxide Utilization (Ed. M. Aresta, J. V. Schloss), NATO ASI Ser. C, 314; Kluwer: Dordrecht, Netherlands, 1990, 23
56. I. Pápai, G. Schubert, I. Mayer, G. Besenyei, M. Aresta, Organometallics 2004, 23, 5252-5259
57. D. C. Graham, C. Mitchell, M. I. Bruce, G. F. Metha, J. H. Bowie, M. A. Buntine, Organometallics 2007, 26, 6784-6792
58. S. Sakaki, K. Mine, D. Taguchi, T. Arai, Bull. Chem. Soc. Jpn. 1993, 66, 3289-3299
59. S. Sakaki, K. Mine, T. Hamada, T. Arai, Bull. Chem. Soc. Jpn. 1995, 68, 1873-1882
60. D. C. Graham, M. I. Bruce, G. F. Metha, J. H. Bowie, M. A. Buntine, J. Organomet. Chem. 2008, 693, 2703-2710
61. J. Li, G. Jia, Z. Lin, Organometallics 2008, 27, 3892-3900;, W. H. Bernskoetter, B. T. Tyler, Organometallics 2011, 30, 520-527.
62. L. Dang, Z. Lin, T. B. Marder, Organometallics 2010, 29, 917-927.
63. E. Graf, W. Leitner, J. Chem. Soc. Chem. Commun. 1992, 623-624
64. T. Burgemeister, F. Kastner, W. Leitner, Angew. Chem. 1993, 105, 781-783
65. Angew. Chem. Int. Ed. Engl. 1993, 32, 739-741
66. W. Leitner, Angew. Chem. 1994, 106, 183-184
67. Angew. Chem. Int. Ed. Engl. 1994, 33, 173-174.
68. F. Hutschka, A. Dedieu, W. Leitner, Angew. Chem. 1995, 107, 1905-1908
69. Angew. Chem. Int. Ed. Engl. 1995, 34, 1742-1745
70. F. Hutschka, A. Dedieu, M. Eichberger, R. Fornika, W. Leitner, J. Am. Chem. Soc. 1997, 119, 4432-4443.
71. N. Fey, A. G. Orpen, J. N. Harvey, Coord. Chem. Rev. 2009, 253, 704-722
72. J. Jover, N. Fey, J. N. Harvey, G. C. Lloyd-Jones, A. G. Orpen, G. J. J. Owen-Smith, Organometallics 2010, 29, 6245-6258.
73. P. A. Evans, Modern Rhodium-Catalyzed Organic Reactions, Wiley-VCH, Weinheim, 2005.
74. W. C. Kaska, S. Nemeh, A. Shirazi, S. Potuznik, Organometallics 1988, 7, 13-15
75. A. Vigalok, Y. Ben-David, D. Milstein, Organometallics 1996, 15, 1839-1844.
76. S. Sakaki, Y. Musashi, J. Chem. Soc. Dalton Trans. 1994, 3047-3054.
77. Y. Musashi, S. Sakaki, J. Am. Chem. Soc. 2002, 124, 7588-7603
78. K.-W. Huang, J. H. Han, C. B. Musgrave, E. Fujita, Organometallics 2007, 26, 508-513.
79. M. Albrecht, G. van Koten, Angew. Chem. 2001, 113, 3866-3898
80. Angew. Chem. Int. Ed. 2001, 40, 3750-3781
81. M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759-1792
82. J. T. Singleton, Tetrahedron 2003, 59, 1837-1857
83. The Chemistry of Pincer Compounds (Eds.:, D. Morales-Morales, C. Jensen,), Elsevier Science, Amsterdam, 2007
84. D. Benito-Garagorri, K. Kirchner, Acc. Chem. Res. 2008, 41, 201-213.
85. Preliminary computational studies on these complexes showed that β-hydride elimination is not likely to occur, which is in agreement with other literature reports, for example, S. Nückel, P. Burger, Organometallics 2001, 20, 4345-4359.
86. J. C. Calabrese, T. Herskobitz, J. B. Tinney, J. Am. Chem. Soc. 1983, 105, 5914-5915.
87. D. F. Shriver, Acc. Chem. Res. 1970, 3, 231-238.
88. R. O. Jones, J. Chem. Phys. 1983, 79, 1885-1890
89. N. W. Alcock, Bonding and Structure: Structural Principles in Inorganic and Organic Chemistry, Ellis Horwood, Chichester, 1990.
90. C. Mealli, R. Hoffmann, A. Stockis, Inorg. Chem. 1984, 23, 56-65
91. R. Caballol, E. S. Marcos, J.-C. Barthelat, J. Phys. Chem. 1987, 91, 1328-1333
92. S. Sakaki, A. Dedieu, Inorg. Chem. 1987, 26, 3278-3284.
93. J. Samannshausen, Dalton Trans. 2011, 40, 136-141.
94. F. Weinhold, J. E. Carpenter, in The Structure of Small Molecules and Ions, (Eds.:, R. Naaman, Z. Vager,), Plenum, 1988, 227-236.
95. R. P. Quirk, J. Yin, L. J. Fetters, R. V. Kastrup, Macromolecules 1992, 25, 2262-2267.
96. V. Grignard, Ann. Chim. 1901, 24, 433-490
97. B. Wirz, W. Kunq, J. Labelled Compd. Radiopharm. 1983, 20, 635-653.
98. DFT-based orbitals/Kohn-Sham orbitals can be used for qualitative interpretations, since these were found to be in good agreement with physical-based calculated orbitals. See, for example:, R. Stowasser, R. Hoffmann, J. Am. Chem. Soc. 1999, 121, 3414-3420.
99. Gaussian 09, Revision A.1, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, A. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
100. S. Grimme, J. Comput. Chem. 2006, 27, 1787-1799.
101. F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305
102. D. Andrae, U. Haeussermann, M. Dolg, H. Stoll, H. Preuss, Theor. Chim. Acta 1990, 77, 123-141.
103. K. Fukui, J. Phys. Chem. 1970, 74, 4161-4163
104. K. Fukui, Acc. Chem. Res. 1981, 14, 363-368
105. C. Gonzalez, H. B. Schlegel, J. Chem. Phys. 1989, 90, 2154-2161
106. C. Gonzalez, H. B. Schlegel, J. Phys. Chem. 1990, 94, 5523-5527.