Synthesis and characterization of carbazolide-based iridium PNP pincer complexes. Mechanistic and computational investigation of alkene hydrogenation: Evidence for an Ir(III)/Ir(V)/Ir(III) catalytic cycle

Journal of the American Chemical Society

Volumn 136, Issue 18, 2014, Pages 6672-6683

  Cheng, Chen ^a   Kim, Bong Gon ^a,c   Guironnet, Damien ^a   Brookhart, Maurice ^a   Guan, Changjian ^b   Wang, David Y ^b   Krogh Jespersen, Karsten ^b   Goldman, Alan S ^b  

^a University of North Carolina at Chapel Hill   (United States)

^b RUTGERS UNIVERSITY   (United States)

^c Gyeongsang National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ETHANE; ETHYLENE; HYDRIDES; HYDROGENATION; IRIDIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

ALKENE HYDROGENATION; CATALYST RESTING STATE; CATALYTIC HYDROGENATION; COMPUTATIONAL INVESTIGATION; ETHYLENE CONCENTRATION; IR COMPLEXES (III); MIGRATORY INSERTION; SYNTHESIS AND CHARACTERIZATIONS;

IRIDIUM;

ALKENE; CARBAZOLE DERIVATIVE; ETHANE; ETHYLENE; ETHYLENE DERIVATIVE; IRIDIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); DENSITY FUNCTIONAL THEORY; HYDROGENATION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 84900337105     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja501572g     Document Type: Article

References (69)

1. Findlater, M.; Choi, J.; Goldman, A. S.; Brookhart, M. Catal. Met. Complexes 2012, 38, 113-141
2. Choi, J.; MacArthur, A. H. R.; Brookhart, M.; Goldman, A. S. Chem. Rev. 2011, 111, 1761-1779
3. Huang, Z.; Brookhart, M.; Goldman, A. S.; Kundu, S.; Ray, A.; Scott, S. L.; Vicente, B. C. Adv. Synth. Catal. 2009, 351, 188-206
4. Morales-Morales, D. Iridium Complexes Org. Synth. 2009, 325-344
5. Xu, W.; Rosini, G. P.; Gupta, M.; Jensen, C. M.; Kaska, W. C.; Krogh-Jespersen, K.; Goldman, A. S. Chem. Commun. 1997, 2273-2274
6. Goldman, A. S.; Roy, A. H.; Huang, Z.; Ahuja, R.; Schinski, W.; Brookhart, M. Science 2006, 312, 257-261
7. Nawara-Hultzsch, A. J.; Hackenberg, J. D.; Punji, B.; Supplee, C.; Emge, T. J.; Bailey, B. C.; Schrock, R. R.; Brookhart, M.; Goldman, A. S. ACS Catal. 2013, 3, 2505-2514
8. Haibach, M. C.; Kundu, S.; Brookhart, M.; Goldman, A. S. Acc. Chem. Res. 2012, 45, 947-958
9. Ahuja, R.; Punji, B.; Findlater, M.; Supplee, C.; Schinski, W.; Brookhart, M.; Goldman, A. S. Nat. Chem. 2011, 3, 167-171
10. Crabtree, R. H.; Mihelcic, J. M.; Quirk, J. M. J. Am. Chem. Soc. 1979, 101, 7738-7739
11. Burk, M. J.; Crabtree, R. H. J. Am. Chem. Soc. 1987, 109, 8025-32
12. Maguire, J. A.; Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1989, 111, 7088-7093
13. Maguire, J. A.; Petrillo, A.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 9492-9498
14. Gupta, M.; Hagen, C.; Flesher, R. J.; Kaska, W. C.; Jensen, C. M. Chem. Commun. 1996, 2083-2084
15. Liu, F.; Goldman, A. S. Chem. Commun. 1999, 655-656
16. Haenel, M. W.; Oevers, S.; Angermund, K.; Kaska, W. C.; Fan, H.-J.; Hall, M. B. Angew. Chem., Int. Ed. 2001, 40, 3596-3600
17. Göttker-Schnetmann, I.; White, P.; Brookhart, M. J. Am. Chem. Soc. 2004, 126, 1804-1811
18. Kuklin, S. A.; Sheloumov, A. M.; Dolgushin, F. M.; Ezernitskaya, M. G.; Peregudov, A. S.; Petrovskii, P. V.; Koridze, A. A. Organometallics 2006, 25, 5466-5476
19. Kundu, S.; Choliy, Y.; Zhuo, G.; Ahuja, R.; Emge, T. J.; Warmuth, R.; Brookhart, M.; Krogh-Jespersen, K.; Goldman, A. S. Organometallics 2009, 28, 5432-5444
20. Punji, B.; Emge, T. J.; Goldman, A. S. Organometallics 2010, 29, 2702-2709
21. Morales-Morales, D.; Redon, R.; Yung, C.; Jensen, C. M. Inorg. Chim. Acta 2004, 357, 2953-2956
22. Göttker-Schnetmann, I.; Brookhart, M. J. Am. Chem. Soc. 2004, 126, 9330-9338
23. Krogh-Jespersen, K.; Czerw, M.; Kanzelberger, M.; Goldman, A. S. J. Chem. Inf. Comput. Sci. 2001, 41, 56-63
24. Krogh-Jespersen, K.; Czerw, M.; Summa, N.; Renkema, K. B.; Achord, P. D.; Goldman, A. S. J. Am. Chem. Soc. 2002, 124, 11404-11416
25. Renkema, K. B.; Kissin, Y. V.; Goldman, A. S. J. Am. Chem. Soc. 2003, 125, 7770-7771
26. Göttker-Schnetmann, I.; White, P. S.; Brookhart, M. Organometallics 2004, 23, 1766-1776
27. Goettker-Schnetmann, I.; Heinekey, D. M.; Brookhart, M. J. Am. Chem. Soc. 2006, 128, 17114-17119
28. Malcolmson, S. J.; Meek, S. J.; Sattely, E. S.; Schrock, R. R.; Hoveyda, A. H. Nature 2008, 456, 933-937
29. Ibrahem, I.; Yu, M.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 3844-3845
30. Flook, M. M.; Jiang, A. J.; Schrock, R. R.; Muller, P.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 7962-7963
31. Wang, D. Y.; Choliy, Y.; Krogh-Jespersen, K.; Hartwig, J. F.; Goldman, A. S. Abstracts of Papers. In Proceedings of the 240th ACS National Meeting, Boston, MA, August 22-26, 2010; ACS: Washington, DC, 2010, INOR-5.
32. Wang, D. Y.; Krogh-Jespersen, K.; Goldman, A. S. Abstracts of Papers. In Proceedings of the 244th ACS National Meeting and Exposition, Philadelphia, PA, August 19-23, 2012; ACS: Washington, DC, 2012, INOR-587.
33. Wang, D. Y. Ph. D. Thesis, Rutgers University: New Brunswick, NJ, 2012. The origin of this effect will be discussed in detail in a forthcoming publication.
34. Ozerov, O. V.; Guo, C.; Papkov, V. A.; Foxman, B. M. J. Am. Chem. Soc. 2004, 126, 4792-4793
35. Weng, W.; Guo, C.; Moura, C.; Yang, L.; Foxman, B. M.; Ozerov, O. V. Organometallics 2005, 24, 3487-3499
36. Gatard, S.; Celenligil-Cetin, R.; Guo, C.; Foxman, B. M.; Ozerov, O. V. J. Am. Chem. Soc. 2006, 128, 2808-2809
37. Weng, W.; Guo, C.; Celenligil-Cetin, R.; Foxman, B. M.; Ozerov, O. V. Chem. Commun. 2006, 197-199
38. a values are in DMSO. Source: http://www.chem.wisc. edu/areas/reich/pkatable/index.htm.
39. Britovsek, G. J. P.; Gibson, V. C.; Hoarau, O. D.; Spitzmesser, S. K.; White, A. J. P.; Williams, D. J. Inorg. Chem. 2003, 42, 3454-3465
40. Lee, D. W.; Kaska, W. C.; Jensen, C. M. Organometallics 1998, 17, 1-3
41. Barbaro, P.; Bianchini, C.; Meli, A.; Peruzzini, M.; Vacca, A.; Vizza, F. Organometallics 1991, 10, 2227-2238
42. Garcia-Camprubi, A.; Martin, M.; Sola, E. Inorg. Chem. 2010, 49, 10649-10657
43. Peverati, R.; Truhlar, D. G. J. Phys. Chem. Lett. 2011, 2, 2810-2817
44. Biswas, S.; Zhou, T.; Wang, D. Y.; Hackenberg, J.; Nawara-Hultzsch, A.; Schrock, R. R.; Brookhart, M.; Krogh-Jespersen, K.; Goldman, A. S. Abstracts of Papers. In Proceedings of the 245th ACS National Meeting and Exposition, New Orleans, LA, April 7-11, 2013; ACS: Washington, DC, 2013, INOR-681. The origin of the kinetic barrier will be discussed in detail in a forthcoming publication.
45. Jean, Y.; Eisenstein, O. Polyhedron 1988, 7, 405-407
46. Riehl, J. F.; Jean, Y.; Eisenstein, O.; Pelissier, M. Organometallics 1992, 11, 729-737
47. The van der Waals radii of Ir and H are reported as 202 and 110 pm, respectively. http://periodic.lanl.gov/index.shtml.
48. Brookhart, M.; Green, M. L. H. J. Organomet. Chem. 1983, 250, 395-408
49. Brookhart, M.; Green, M. L. H.; Parkin, G. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 6908-6914
50. See, e.g. Bersuker, I. B. The Jahn-Teller Effect: Implications in Electronic Structure Calculations. In Progress in Theoretical Chemistry and Physics; Piecuch, P.; Maruani, J.; Delgado-Barrio, G.; Wilson, S., Eds.; Springer: New York, 2009; Vol. 19; pp 343-362.
51. The barrier predicted by M11-L (23.6 kcal/mol) is in fact very close to the experimental value (21 kcal/mol). We note that M11-L is intended to ... provide broad accuracy for both single-configurational and multiconfigurational molecules and for solid-state lattice constants. Peverati, R.; Truhlar, D. C. J. Phys. Chem. Lett. 2012, 3, 117-124
52. Wick, D. D.; Goldberg, K. I. J. Am. Chem. Soc. 1997, 119, 10235-10236
53. Bartlett, K. L.; Goldberg, K. I.; Borden, W. T. J. Am. Chem. Soc. 2000, 122, 1456-1465
54. Bartlett, K. L.; Goldberg, K. I.; Borden, W. T. Organometallics 2001, 20, 2669-2678
55. Fekl, U.; Goldberg, K. I. J. Am. Chem. Soc. 2002, 124, 6804-6805
56. Elliot, A. J.; McCracken, D. R.; Buxton, G. V.; Wood, N. D. J. Chem. Soc. Faraday Trans. 1990, 86, 1539-1547
57. Perutz, R. N.; Sabo-Etienne, S. Angew. Chem., Int. Ed. 2007, 46, 2578-2592
58. Campos, J.; Kundu, S.; Pahls, D. R.; Brookhart, M.; Carmona, E.; Cundari, T. R. J. Am. Chem. Soc. 2013, 135, 1217-1220
59. Saillard, J.; Hoffmann, R. J. Am. Chem. Soc. 1984, 106, 2006-2026
60. Lundquist, E. G.; Huffman, J. C.; Folting, K.; Caulton, K. G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1165-1167
61. Crabtree, R. Acc. Chem. Res. 1979, 12, 331-337
62. Brandt, P.; Hedberg, C.; Andersson, P. G. Chem.-Eur. J. 2003, 9, 339-347
63. Helmchen, G. n.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336-345
64. Cui, X.; Fan, Y.; Hall, M. B.; Burgess, K. Chem.-Eur. J. 2005, 11, 6859-6868
65. Bianchini, C.; Farnetti, E.; Graziani, M.; Kaspar, J.; Vizza, F. J. Am. Chem. Soc. 1993, 115, 1753-1759
66. Onderdelinden, A. L.; van der Ent, A. Inorg. Chim. Acta 1972, 420-426
67. Andrae, D.; Haeussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123-41
68. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
69. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639