Mechanism of Pd(OAc)2/pyridine catalyst reoxidation by O 2: Influence of labile monodentate ligands and identification of a biomimetic mechanism for O2 activation

Chemistry - A European Journal

Volumn 15, Issue 12, 2009, Pages 2915-2922

  Popp, Brian V ^a   Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Density functional calculations; Dioxygen ligands; Homogeneous catalysis; Oxidation palladium

Indexed keywords

BIOMIMETICS; CATALYSIS; CATALYSTS; DENSITY FUNCTIONAL THEORY; HYDROGEN; LIGANDS; OXIDATION; PRECIOUS METALS; PYRIDINE; REACTION KINETICS;

ACETATE LIGANDS; AEROBIC OXIDATIONS; ATOM ABSTRACTIONS; BIO-MIMETIC; BIOLOGICAL OXIDATIONS; CATALYTIC CYCLES; COORDINATION SITES; DENSITY FUNCTIONAL CALCULATIONS; DIOXYGEN LIGANDS; H-BONDS; HOMOGENEOUS CATALYSIS; HYDRIDE SPECIES; HYDROPEROXIDE; MIGRATORY INSERTIONS; MONODENTATE LIGANDS; OXIDATIVE ADDITIONS; PYRIDINE CATALYSTS; RE OXIDATIONS; REDUCTIVE ELIMINATIONS;

PALLADIUM;

LIGAND; OXYGEN; PALLADIUM; PYRIDINE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

CATALYSIS; LIGANDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; OXYGEN; PALLADIUM; PYRIDINES;

EID: 62349094304     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802311     Document Type: Article

References (96)

1. For recent reviews, see: a) S. S. Stahl, Science 2005, 309, 1824-1826;
2. b)S. S. Stahl, Angew. Chem. 2004, 116, 3480-3501;
3. Angew. Chem. Int. Ed. 2004, 43, 3400-3420;
4. c) M. S. Sigman, D. R. Jensen, Acc. Chem. Res. 2006, 39, 221-229;
5. d) B. M. Stoltz, Chem. Lett. 2004, 33, 362-367;
6. e) T. Nishimura, S. Uemura, Synlett 2004, 201-216;
7. f) R. A. Sheldon, I. W. C. E. Arends, G.-J. ten Brink, A. Dijksman, Acc. Chem. Res 2002, 35, 774-781;
8. g) M. Toyota, M. Ihara, Synlett 2002, 1211-1222.
9. a) M. M. Konnick, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 5753-5762;
10. b) M. M. Konnick, B. A. Gandhi, I. A. Guzei, S. S. Stahl, Angew. Chem. 2006, 118, 2970-2973;
11. Angew. Chem. Int. Ed. 2006, 45, 2904-2907;
12. c) M. C. Denney, N. A. Smythe, K. L. Cetto, R. A. Kemp, K. I. Goldberg, J. Am. Chem. Soc. 2006, 128, 2508-2509;
13. d) M. M. Konnick, I. A. Guzei, S. S. Stahl, J. Am. Chem. Soc. 2004, 126, 10212-10213;
14. e) S. S. Stahl, J. L. Thorman, R. C. Nelson, M. A. Kozee, J. Am. Chem. Soc. 2001, 123, 7188-7189.
15. a) B. V. Popp, S. S. Stahl, J. Am. Chem. Soc. 2007, 129, 4410-4422;
16. b) B. V. Popp, J. E. Wendlandt, C. R. Landis, S. S. Stahl, Angew. Chem. 2007, 119, 607-610;
17. Angew. Chem. Int. Ed. 2007, 46, 601-604;
18. c) C. R. Landis, C. M. Morales, S. S. Stahl, J. Am. Chem. Soc. 2004, 126, 16302-16303.
19. a) J. M. Keith, R. J. Nielsen, J. Oxgaard, W. A. Goddard, III, J. Am. Chem. Soc. 2005, 127, 13172-13179;
20. b) T. Privalov, C. Linde, K. Zetterberg, C. Moberg, Organometallics 2005, 24, 885-893;
21. c) R. J. Nielsen, W. A. Goddard III, J. Am. Chem. Soc. 2006, 128, 9651-9660;
22. d) J. M. Keith, R. P. Müller, R. A. Kemp, K. I. Goldberg, W. A. Goddard III, J. Oxgaard, Inorg. Chem. 2006, 45, 9631 - 9633;
23. e) J. M. Keith, W. A. Goddard III, J. Oxgaard, J. Am. Chem. Soc. 2007, 129, 10361-10369;
24. f) S. Chowdhury, I. Rivalta, N. Russo, E. Sicilia, Chem. Phys. Lett. 2007, 443, 183-189;
25. g) S. Chowdhury, I. Rivalta, N. Russo, E. Sicilia, Chem. Phys. Lett. 2008, 456, 41-46;
26. h) S. Chowdhury, I. Rivalta, N. Russo, E. Sicilia, J. Chem. Theory Comput. 2008, 4, 1283-1292.
27. For recent reviews and a highlight on the proposed mechanisms of aerobic oxidation of reduced Pd, see : a) B. V. Popp, S. S. Stahl, Top. Organomet. Chem. 2007, 22, 149-189;
28. b) K. M. Gligorich, M. S. Sigman, Angew. Chem. 2006, 118, 6764-6767;
29. Angew. Chem. Int. Ed. 2006, 45, 6612-6615;
30. c) J. Muzart, Chem. Asian J. 2006, 1, 508-515.
31. For a recent review of such species, including a discussion of their relevance to Pd-catalyzed aerobic oxidation catalysis, see ref. [5a].
32. For leading references, see: a) R. C. Larock, T. R. Hightower, J. Org. Chem. 1993, 58, 5298-5300;
33. b) R. A. T. M. van Benthem, H. Hiemstra, J. J. Michels, W. N. Speckamp, J. Chem. Soc. Chem. Commun. 1994, 357-359;
34. c) R. A. T. M. van Benthem, H. Hiemstra, G. R. Longarela, W. N. Speckamp, Tetrahedron Lett. 1994, 35, 9281 - 9284;
35. d) R. C. Larock, T. R. Hightower, L. A. Hasvold, K. P. Peterson, J. Org. Chem. 1996, 61, 3584-3585;
36. e) W. Zierkiewicz, T. Privalov, Organometallics 2005, 24, 6019-6028;
37. f) B. A. Steinhoff, S. S. Stahl, J. Am. Chem. Soc. 2006, 128, 4348-4355.
38. See refs. [1b,e] and the following leading references: a) T. Nishimura, T. Onoue, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64, 6750-6755;
39. b) S. R. Fix, J. L. Brice, S. S. Stahl, Angew. Chem. 2002, 114, 172-174;
40. Angew. Chem. Int. Ed. 2002, 41, 164-166;
41. c) R. M. Trend, Y. K. Ramtohul, E. M. Ferreira, B. M. Stoltz, Angew. Chem. 2003, 115, 2998-3001;
42. Angew. Chem Int. Ed. 2003, 42, 2892-2895;
43. d) B. A. Steinhoff, I. A. Guzei, S. S. Stahl, J. Am. Chem Soc. 2004, 126, 11268-11278;
44. e) R. M. Trend, Y. K. Ramtohul, B. M. Stoltz, J. Am. Chem. Soc. 2005, 127, 17778-17788.
45. Previous DFT computational, studies of this catalyst system emphasized the mechanism of PdII-mediated oxidation of alcohols, see: a) M. J. Schultz, R. S. Adler, W. Zierkiewicz, T. Privalov, M. S. Sigman, J. Am. Chem. Soc. 2005, 127, 8499-8507;
46. b) reference [4c].
47. Experimental examples of pyridine-coordinated Pd-hydride species have not been reported, but analogous complexes bearing phosphine ligands have been shown to exist in the trans configuration; a) V. V. Grushin, Chem. Rev. 1996, 96, 2011-2033, and references therein;
48. b) I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 13178-13179.
49. Recent DFT studies have identified a similar favorable role for bidentate carboxylate ligands that serve to stabilize monoligated-Pd species involved in non-oxidative Pd°-based catalytic reactions. For representative recent studies, see: a) L. J. Goossen, D. Koley, H. L. Hermann, W. Thiel, J. Am. Chem. Soc. 2005, 127, 11102-11114;
50. b) L. J. Goossen, D. Koley, H. L. Hermann, W. Thiel, Organometallics 2005, 24, 2398-2410;
51. c) M. Ahlquist, P. Fristrup, D. Tanner, P. O. Norrby, Organometallics 2006, 25, 2066-2073;
52. d) M. Ahlquist, G. Fabrizi, S. Cacchi, P. O. Norrby, J. Am. Chem. Soc. 2006, 128, 12785-12793.
53. Reductive elimination of AcOH from a structurally similar T-shaped (NHC)Pd(H)OAc has been, identified, see reference [4c].
54. a) L. Vaska, Science 1963, 140, 809-810;
55. b) L. Vaska, L. S. Chen, C. V. Senoff. Science 1971, 174, 587-589;
56. c) L. Vaska, Acc. Chem. Res. 1976, 9, 175-185.
57. With no electronic barrier for this step, the only barrier would arise from entropy contributions to the free energy.
58. TS relative to the intermediates 18 and 20 is a result of: 1) a very flat gas-phase total-energy surface and 2) the application of solvation free-energy corrections on gas-phase optimized free energies.
59. J. S. Valentine, Chem. Rev. 1973, 73, 235-245.
60. 2 activation in biological systems, see: a) Biological Inorganic Chemistry: Structure and Reactivity (Eds.: H. B. Gray, E. I. Stiefel, J. S. Valentine, I. Bertini), University Science Books, Sausalito, 2007.
61. For representative examples, see: a) B. Shaanan, Nature 1982, 296, 683-684;
62. b) J. P. Coliman, R. Boulatov, C. J. Sunderland, L. Fu, Chem. Rev. 2004, 104, 561-588, and references therein;
63. c) Cytochrome P450: structure, mechanism, and biochemistry, 3rd éd. (Ed.: P. R. Ortiz de Montellano), Kluwer Academic/Plenum Publishers, New York, 2005;
64. d) J. M. Bollinger, Jr., C. Krebs, Curr. Opin. Chem. Biol. 2007, 11, 151-158;
65. e) A. Decker, E.I. Solomon, Curr. Opin. Chem Biol. 2005, 9, 152-163;
66. f) J. P. Klinman, Chem. Rev. 1996, 96, 2541.-2561.
67. a) S. Y. Reece, J. M. Hodgkiss, J. Stubbe, D. G. Nocera, Philos. Trans. R. Soc. London Ser. B 2006, 361, 1351-1364;
68. b) J. Rosenthal, D. G. Nocera, Acc. Chem. Res. 2007, 40, 543-553.
69. Gaussian 03, Revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, 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, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
70. C. Catlett, W. E. Allcock, P. Andrews, R. Aydt, R. Bair, N. Balac, B. Banister, T. Barker, M. Bartelt, P. Beckman, F. Berman, G. Bertoline, A. Blatecky, J. Boisseau, J. Bottum, S. Brunett, J. Bunn, M. Butler, D. Carver, J. Cobb, T. Cockerill, P.F. Couvares, M. Dahan, D. Diehl, T. Dunning, I. Foster, K. Gaither, D. Gannon, S. Goasguen, M. Grobe, D. Hart, M. Heinzel, C. Hempel, W. Huntoon, J. Insley, C. Jordan, I. Judson, A. Kamrath, N. Karonis, C. Kesselman, P. Kovatch, L. Lane, S. Lathrop, M. Levine, D. Lika, L. Liming, M. Livny, R. Loft, D. Marcusiu, Jim Marsteller, S. Martin, S. McCaulay, J. McGee, L. McGinnis, M. McRobbie, P. Messina, R. Moore, R. Moore, J. P. Navarro, J. Nichols, M. E. Papka, R. Pennington, G. Pike, J. Pool, R. Reddy, D. Reed, T. Rimovsky, E. Roberts, R. Roskies, S. Sanielevici, J. R. Scott, A. Shankar, M. Sheddon, M. Showerman, D. Simmel, A. Singer, D. Skow, S. Smallen, W. Smith, C. Song, R. Stevens, C. Stewart, R. B. Stock, N. Stone, J. Towns, T. Urban, M. Vildibill, E. Walker, V. Welch, N. Wilkins-Diehr, R. Williams, L. Winkler, L. Zhao, A. Zimmerman, in High performance computing and grids in action (Ed.: L. Grandinetti), IOS Press, Amsterdam, 2008, pp. 225-249.
71. W. Koch, M. C. Holthausen, A Chemist's Guide to Density Functional Theory, Wiley-VCH, Weinheim, 2000.
72. A. D. Becke, J. Chem. Phys. 1993, 98, 1372-1377.
73. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
74. a) The Stuttgart RSC 1.997 ECP basis set for Pd was obtained from the Extensible Computational Chemistry Environment Basis Set Database, Version 02/25/04, as developed and distributed by the Molecular Science Computing Facility, Environmental and Molecular Sciences Laboratory which is part of the Pacific Northwest Laboratory, P. O. Box 999, Richland, Washington 99352, USA, and funded by the U.S. Department of Energy. The Pacific Northwest Laboratory is a multi-program laboratory operated by Battelle Memorial Institute for the U.S. Department of Energy under contract DE-AC0676RLO 1830. Contact Karen Schuchardt for further information; b) D. Andrae, U. Häußermann, M. DoIg, H. Stoll, H. Preuß, Theor. Chim. Acta 1990, 77, 123-141.
75. W. J. Hehre, L. Radom, L. P. v. R. Schleyer, J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
76. a) C. Y. Peng, P. Y. Ayala, H. B. Schlegel, M. J. Frisch, J. Comput. Chem. 1996, 17, 49-56;
77. b) C. Y. Peng, H. B. Schlegel, Isr. J. Chem. 1993, 33, 449-454.
78. a) C. Gonzalez, H. B. Schlegel, J. Chem. Phys. 1989, 90, 2154-2161;
79. b) C. Gonzalez, H. B. Schlegel, J. Phys. Chem. 1990, 94, 5523-5527.
80. For an overview of solvation models and reviews on PCM. methods, see: a) J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999-3093;
81. b) C. J. Cramer, D. G. Truhlar, Chem. Rev. 1999, 99, 2161-2200;
82. For references on our current approach, see: c) E. Canees, B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 107, 3032-3041;
83. d) B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 106, 5151-5158;
84. e) B. Mennucci, E. Caneès, J. Tomasi, J. Phys Chem. B 1997, 101, 10506-10517;
85. f) J. Tomasi, B. Mennucci, E. Caneès, J. Mol. Struct. 1999, 464, 211-226.
86. D. R. Lide, Handbook of Chemistry and Physics, 88th ed., CRC Press, Boca Raton, 2007.
87. M.E. Kandil, K.N. Marsh, A.R.H. Goodwin, J. Chem. Eng. Data 2008, 53, 1056-1065.
88. M. O. McLinden, J. D. Splett, J. Res. Natl. Inst. Stand. Technol. 2008, 113, 29-67.
89. C. J. Cramer, Essentials of Computational Chemistry: theories and models, Wiley, New York, 2002, pp. 341-342.
90. A. E. Reed, R. B. Weinstock, F. Weinhold, J. Chem. Phys 1985, 83, 735-746.
91. A. A. Ovchinnikov, J. K. Labanowski, Phys. Rev. A 1996, 53, 3946-3952.
92. L. Noodleman, J. Chem. Phys 1981, 74, 5737-5743.
93. I. Ciofini, C. A. Daul, Coord. Chem. Rev. 2003, 238-239, 187-209.
94. There has been significant recent discussion about the accuracy of computational predictions of spin-state energy differences between OST and OSS species using the B3LY.P functional incorporating 20% exact Hartree-Fock (HF) exchange (default setting in Gaussian 03). For an excellent overview, see: J. N. Harvey, Ann. Rep. Sec. C 2006, 102, 203-226, and references therein.
95. 2 species should be carried out in the near future; see for example, C. J. Cramer, J. R. Gour, A. Kinal, M. Wtoch, P. Piecuch, A. R. M. Shahi, L. Gagliardi, J. Phys. Chem. A 2008, 112, 3754-3767.
96. The current approach yields an upper limit to the energy of the MECP. This energy can be more rigorously established using the methods of Harvey etal., see for example: J. N. Harvey, M. Aschi, H. Schwarz, W. Koch, Theor. Chem. Acc. 1998, 99, 95-99.