A mechanistic change results in 100 times faster CH functionalization for ethane versus methane by a homogeneous Pt catalyst

Journal of the American Chemical Society

Volumn 136, Issue 28, 2014, Pages 10085-10094

  Konnick, Michael M ^a   Bischof, Steven M ^a   Yousufuddin, Muhammed ^b   Hashiguchi, Brian G ^a   Ess, Daniel H ^c   Periana, Roy A ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

^c Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC OXIDATION; CHEMICAL ACTIVATION; ESTERIFICATION; ESTERS; ETHANE; ETHANOL; ETHYLENE; HYDRIDES; METHANE;

C-H FUNCTIONALIZATION; CATALYTIC CYCLES; FUNCTIONALIZATIONS; HYDRIDE ELIMINATION; LOW TEMPERATURES; ORGANIC REACTION; OXIDATIVE FUNCTIONALIZATION; QUANTUM-MECHANICAL CALCULATION;

PLATINUM;

ESTER; ETHANE; ETHYLENE; ISETHIONIC ACID; METHANE; PLATINUM; SULFURIC ACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; COMPARATIVE STUDY; CONTROLLED STUDY; COVALENT BOND; DECOMPOSITION; ELECTROPHILICITY; FUNCTIONALIZATION; OXIDATION; QUANTUM MECHANICS; REACTION ANALYSIS; REACTION TIME; STEADY STATE;

EID: 84904430768     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja504368r     Document Type: Article

References (64)

1. U.S. Energy Information Administration. U.S. Crude Oil and Natural Gas Proved Reserves, 2011, 2013.
2. George, D. L.; Bowles, E. B., Jr. Pipeline Gas J. 2011, 238, 38
3. Haggin, J. Chem. Eng. News 1993, 71 (34) 21-22
4. Periana, R. A.; Bhalla, G.; Tenn, W. J.; Young, K. J. H.; Liu, X. Y.; Mironov, O.; Jones, C. J.; Ziatdinov, V. R. J. Mol. Catal. A-Chem. 2004, 220, 7
5. Conley, B. L.; Tenn, W. J.; Young, K. J. H.; Ganesh, S. K.; Meier, S. K.; Ziatdinov, V. R.; Mironov, O.; Oxgaard, J.; Gonzales, J.; Goddard, W. A.; Periana, R. A. J. Mol. Catal. A-Chem. 2006, 251, 8
6. Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879
7. Chepaikin, E. G. Russ Chem. Rev. 2011, 80, 363
8. Lersch, M.; Tilset, M. Chem. Rev. 2005, 105, 2471
9. Crabtree, R. H. J. Chem. Soc., Dalton Trans. 2001, 2951
10. Schwarz, H. Angew. Chem., Int. Ed. 2011, 50, 10096
11. Hashiguchi, B. G.; Bischof, S. M.; Konnick, M. M.; Periana, R. A. Acc. Chem. Res. 2012, 45, 885
12. Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560
13. Gol'dshleger, N. F.; Es'kova, V. V.; Shteinman, A. A.; Shilov, A. E. Russ J. Phys. Ch. USSR 1972, 46, 785
14. Chen, G. S.; Labinger, J. A.; Bercaw, J. E. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 6915
15. Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507
16. Rostovtsev, V. V.; Labinger, J. A.; Bercaw, J. E.; Lasseter, T. L.; Goldberg, K. I. Organometallics 1998, 17, 4530
17. Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1995, 117, 9371
18. Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 5961
19. Fekl, U.; Goldberg, K. I. Adv. Inorg. Chem. 2003, 54, 259
20. Pawlikowski, A. V.; Getty, A. D.; Goldberg, K. I. J. Am. Chem. Soc. 2007, 129, 10382
21. Khusnutdinova, J. R.; Zavalij, P. Y.; Vedernikov, A. N. Organometallics 2007, 26, 3466
22. Vedernikov, A. N. Curr. Org. Chem. 2007, 11, 1401
23. Vedernikov, A. N.; Binfield, S. A.; Zavalij, P. Y.; Khusnutdinova, J. R. J. Am. Chem. Soc. 2006, 128, 82
24. Yahav-Levi, A.; Goldberg, I.; Vigalok, A.; Vedernikov, A. N. J. Am. Chem. Soc. 2008, 130, 724
25. Baik, M. H.; Newcomb, M.; Friesner, R. A.; Lippard, S. J. Chem. Rev. 2003, 103, 2385
26. Sen, A. Acc. Chem. Res. 1998, 31, 550
27. Butikofer, J. L.; Parson, T. G.; Roddick, D. M. Organometallics 2006, 25, 6108
28. Periana, R. A.; Mironov, O.; Taube, D.; Bhalla, G.; Jones, C. J. Science 2003, 301, 814
29. Periana, R. A.; Taube, D. J.; Evitt, E. R.; Loffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340
30. Zerella, M.; Mukhopadhyay, S.; Bell, A. T. Chem. Commun. 2004, 1948
31. De Vos, D. E.; Sels, B. E. Angew. Chem., Int. Ed. 2005, 44, 30
32. Mironov, O. A.; Bischof, S. M.; Konnick, M. M.; Hashiguchi, B. G.; Ziatdinov, V. R.; Goddard, W. A., III; Ahlquist, M.; Periana, R. A. J. Am. Chem. Soc. 2013, 135, 14644
33. Lodgsdon, J. E. In Encyclopedia of Chemical Technology 9, 4 th ed.; Howe-Grant, M.; Kirk, R. E.; Othmer, D. F.; Kroschwitz, J. I., Eds.; Wiley: New York, 1991; p 817.
34. Labinger, J. A. In Alkane C-H Activation by Single-Site Metal Catalysis; Pérez, P. J., Ed.; Springer: New York, 2012; Vol. 38, p 17.
35. Kosswig, K. Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, 2000; Vol. A25, p 747.
36. Kosswig, K. Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim 2000; Vol. A25, p 503.
37. Brooks, B. T.; Humphrey, I. J. Am. Chem. Soc. 1918, 40, 822
38. Michael, A.; Weiner, N. J. Am. Chem. Soc. 1936, 58, 294
39. Bordwell, F. G.; Suter, C. M.; Webber, A. J. J. Am. Chem. Soc. 1945, 67, 827
40. Bordwell, F. G.; Rondestvedt, C. S. J. Am. Chem. Soc. 1948, 70, 2429
41. Bordwell, F. G.; Peterson, M. L. J. Am. Chem. Soc. 1954, 76, 3952
42. Bordwell, F. G.; Peterson, M. L. J. Am. Chem. Soc. 1954, 76, 3957
43. Bordwell, F. G.; Peterson, M. L.; Rondestvedt, C. S. J. Am. Chem. Soc. 1954, 76, 3945
44. Sen, A.; Benvenuto, M. A.; Lin, M. R.; Hutson, A. C.; Basickes, N. J. Am. Chem. Soc. 1994, 116, 998
45. Bass, S. J.; Gillespie, R. J.; Robinson, E. A. J. Chem. Soc. 1960, 821
46. Gillespie, R. J. J. Chem. Soc. 1950, 2493
47. Gillespie, R. J.; Robinson, E. A.; Solomons, C. J. Chem. Soc. 1960, 4320
48. Basickes, N.; Hogan, T. E.; Sen, A. J. Am. Chem. Soc. 1996, 118, 13111
49. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 5 th ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2009.
50. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Sausalito, CA, 1987.
51. Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681
52. Gilbert, T. M.; Hristov, I.; Ziegler, T. Organometallics 2001, 20, 1183
53. Hristov, I. H.; Ziegler, T. Organometallics 2003, 22, 1668
54. Paul, A.; Musgrave, C. B. Organometallics 2007, 26, 793
55. Ahlquist, M.; Periana, R. A.; Goddard, W. A. Chem. Commun. 2009, 2373
56. Kiernan, P. M.; Ludi, A. J. Chem. Soc., Dalton Trans. 1978, 1127
57. Connick, W. B.; Marsh, R. E.; Schaefer, W. P.; Gray, H. B. Inorg. Chem. 1997, 36, 913
58. Bruce, J.; Johnson, D.; Cordes, W.; Sadoski, R. J. Chem. Crystallogr. 1997, 27, 695
59. Clark, H. C.; Manzer, L. E. J. Organomet. Chem. 1973, 59, 411
60. Shiotsuki, M.; White, P. S.; Brookhart, M.; Templeton, J. L. J. Am. Chem. Soc. 2007, 129, 4058
61. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Menucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomassi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision B.01; Gaussian, Inc.: Wallingford, CT, 2009.
62. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
63. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
64. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378