Hydrogenation of dimethyl carbonate to methanol by trans -[Ru(H) 2(PNN)(CO)] catalysts: DFT evidence for ion-pair-mediated metathesis paths for C-OMe bond cleavage

Organometallics

Volumn 32, Issue 23, 2013, Pages 6969-6985

  Hasanayn, Faraj ^a   Baroudi, Abdulkader ^a   Bengali, Ashfaq A ^b   Goldman, Alan S ^c  

^a AMERICAN UNIVERSITY OF BEIRUT   (Lebanon)

^b TEXAS A AND M UNIVERSITY AT QATAR   (Qatar)

^c RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL GROUPS; DIMETHYL CARBONATE; HYDRIDE TRANSFERS; ION PAIR FORMATION; METHANOL MOLECULES; PINCER COMPLEXES; POLARIZABLE CONTINUUMS; REACTION PATHWAYS;

CATALYSTS; HYDRIDES; HYDROGENATION; IONS; LIGANDS; METALS; METHANOL; ORGANIC SOLVENTS; PHOSPHORUS COMPOUNDS; REACTION INTERMEDIATES; SPHERES;

RUTHENIUM;

EID: 84890335568     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om4005127     Document Type: Article

References (145)

1. de Vries, J. G.; Elsevier, C. J. The Handbook of Homogeneous Hydrogenation; Wiley-VCH: Weinheim, Germany, 2007.
2. Noyori, R.; Hashiguchi, S. In Applied Homogeneous Catalysis with Organometallic Compounds; Wiley-VCH: New York, 2008.
3. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
4. Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G. J. Chem. Soc. A 1966, 1711
5. Bhaduri, S.;; Mukesh, D. Homogeneous Catalysis; Wiley, New York, 2000.
6. Hartwig, J. F. In Organotransition Metal Chemistry; University Science Books: Sausalito, CA, 2010; p 575.
7. Knowles, W. S.; Noyori, R. Acc. Chem. Res. 2007, 40, 1238 and articles in this thematic issue
8. Blum, Y.; Czarkie, D.; Rahamim, Y.; Shvo, Y. Organometallics 1985, 4, 1459
9. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97
10. Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008
11. Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord. Chem. Rev. 2004, 248, 2201
12. Joseph, S. M.; Samec, J. S.; Backvall, J.-E.; Andersson, P. G. Chem. Soc. Rev. 2006, 35, 237
13. Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681
14. Eisenstein, O.; Crabtree, R. H. New. J. Chem. 2013, 37, 21
15. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8.
16. Seyden-Penne, J. Reductions by the Alumino- and Borohydrides in Organic Synthesis, 2 nd ed.; Wiley: New York, 1997.
17. Gribble, G. W. Chem. Soc. Rev. 1998, 27, 395
18. Milstein, D. Top. Catal. 2010, 53, 915
19. Gunanathan, C.; Milstein, D. Top. Organomet. Chem. 2011, 37, 55
20. Ito, M.; Ootsuka, T.; Watari, R.; Shiibashi, A.; Himizu, A.; Ikariya, T. J. Am. Chem. Soc. 2011, 133, 4240
21. Dub, P. A.; Ikariya, T. ACS Catal. 2012, 2, 1718
22. Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2006, 45, 1113
23. Balaraman, E.; Gnanaprakasam, B.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2010, 132, 16756
24. Gunanathan, C.; Milstein, D. Acc. Chem. Res. 2011, 44, 588
25. Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 2005, 127, 10840
26. Gunanathan, C.; Ben-David, Y.; Milstein, D. Science 2007, 317, 790
27. Zeng, H.; Guan, Z. J. Am. Chem. Soc. 2011, 133, 1159
28. Gnanaprakasam, B.; Balaraman, E.; Gunanathan, C.; Milstein, D. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 1755
29. Balaraman, E.; Gunanathan, C.; Zhang, J.; Shimon, L. J. W.; Milstein, D. Nat. Chem. 2011, 3, 609
30. Balaraman, E.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50, 11702
31. Sakakura, T.; Kohno, K. Chem. Commun. 2009, 45, 1312
32. Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365
33. Olah, G. A.; Goeppert, A.; Prakash, G. K. S. Beyond Oil and Gas: The Methanol Economy; Wiley-VCH: Weinheim, Germany, 2006.
34. Centi, G.; Quadrelli, E. A.; Perathoner, S. Energy Environ. Sci. 2013, 6, 1711
35. Huff, C. A.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18122
36. Baratta, W.; Chelucci, G.; Gladiali, S.; Siega, K.; Toniutti, M.; Zanette, M.; Zangrando, E.; Rigo, P. Angew. Chem., Int. Ed. 2005, 44, 6214
37. Baratta, W.; Bosco, M.; Chelucci, G.; Del Zotto, A.; Siega, K.; Toniutti, M.; Zangrando, E.; Rigo, P. Organometallics 2006, 25, 4611
38. Baratta, W.; Ballico, M.; Esposito, G.; Rigo, P. Chem. Eur. J. 2008, 14, 558
39. Hamilton, R. J.; Leong, C. G.; Bigam, G.; Miskolzie, M.; Bergens, S. H. J. Am. Chem. Soc. 2005, 127, 4152
40. Hamilton, R. J.; Bergens, S. H. J. Am. Chem. Soc. 2006, 128, 13700
41. Hamilton, R. J.; Bergens, S. H. J. Am. Chem. Soc. 2008, 130, 11979
42. Takebayashi, S.; Dabral, N.; Miskolzie, M.; Bergens, S. H. J. Am. Chem. Soc. 2011, 133, 9666
43. Bertoli, M.; Choualeb, A.; Lough, A. J.; Moore, B.; Spasyuk, D.; Gusev, D. G. Organometallics 2011, 30, 3479
44. Spasyuk, D.; Gusev, D. G. Organometallics 2012, 31, 5239
45. Takebayashi, S.; Bergens, S. H. Organometallics 2009, 28, 2349
46. Darensbourg, D. J.; Rokicki, A.; Darensbourg, M. Y. J. Am. Chem. Soc. 1981, 103, 3223
47. Darensbourg, D. J.; Kudaroski, R.; Bauch, C. G.; Pala, M.; Simmons, D.; White, J. N. J. Am. Chem. Soc. 1985, 107, 7463
48. Darensbourg, D. J.; Kyran, S. J.; Yeung, A. D.; Bengali, A. A. Eur. J. Inorg. Chem. 2013, 4024
49. Whittlesey, M. K.; Perutz, R. N.; Moore, M. H. Organometallics 1996, 15, 5166
50. Salem, H.; Shimon, L. J. W.; Diskin-Posner, Y.; Leitus, G.; Ben-David, Y.; Milstein, D. Organometallics 2009, 28, 4791
51. Langer, R.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50, 9948
52. Schmeier, T. J.; Dobereiner, G. E.; Crabtree, R. H.; Hazari, N. J. Am. Chem. Soc. 2011, 133, 9274
53. Li, H.; Wen, M.; Wang, Z.-X. Inorg. Chem. 2012, 51, 5716
54. Yang, X. ACS Catal. 2012, 2, 964
55. Hasanayn, F.; Baroudi, A. Organometallics 2013, 32, 2493
56. Frisch, M. J., Gaussian 09, Rev. A.02; Gaussian, Inc., Wallingford, CT, 2009.
57. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
58. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639
59. Raghavachari, K.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
60. Rassolov, V. A.; Ratner, M. A.; Pople, J. A.; Redfern, P. C.; Curtiss, L. A. J. Comput. Chem. 2001, 22, 976
61. Hay, P. J; Wadt, W. R. J. Chem. Phys. 1985, 82, 279
62. Höllwarth, A.; Böhlers, A. W.; Bohme, M.; Dapprich, S.; Gobbi, A.; Hollwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111
63. See: https://bse.pnl.gov/bse/portal.
64. Chai, J.-D.; Head-Gordon, M. Phys. Chem. Chem. Phys. 2008, 10, 6615
65. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027
66. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43
67. Hehre, J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
68. Ben-Naim, A.; Marcus, Y. J. Chem. Phys. 1984, 81, 2016
69. Hermans, J.; Wang, L. J. Am. Chem. Soc. 1997, 119, 2707
70. Tissandier, M. D.; Cowen, K. A.; Feng, W. Y.; Gundlach, E.; Cohen, M. H.; Earhart, A. D.; Coe, J. V.; Tuttle, T. R. J. Phys. Chem. A 1998, 102, 7787
71. Kelly, C. P.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2006, 110, 16066
72. Lopes, P. E. M.; Roux, B.; MacKerell, A. D. Theor. Chem. Acc. 2009, 124, 11
73. Chen, Y.; Ye, S.; Jiao, L.; Liang, Y.; Sinha-Mahapatra, D. K.; Herndon, J. W.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 10773
74. Wiberg, K. B.; Morgan, K. M.; Maltz, H. J. Am. Chem. Soc. 1994, 116, 11067
75. Li, H.; Wang, X.; Huang, F.; Lu, G.; Jiang, J.; Wang, Z.-X. Organometallics 2011, 30, 5233
76. Clapham, S. E.; Guo, R.; Zimmer-De Iuliis, M.; Rasool, N.; Lough, A.; Morris, R. H. Organometallics 2006, 25, 5477
77. Burn, M. J.; Fickes, M. G.; Hollander, F. J.; Bergman, R. G. Organometallics 1995, 14, 137
78. Basolo, F.; Pearson, R. G. Prog. Inorg. Chem. 1962, 4, 381
79. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335
80. Coe, B. J.; Glenwright, S. J. Coord. Chem. Rev. 2000, 203, 5
81. Appleton, T. G.; Bennett, M. A. Inorg. Chem. 1978, 17, 738
82. Appleton, T. G.; Hall, J. R.; Ralph, S. F. Inorg. Chem. 1985, 24, 4685
83. Weinhold, F.; Landis, C. R. Valency and bonding: a natural bond orbital donor-acceptor perspective; Cambridge University Press: Cambridge, U.K., 2005.
84. Chen, H-Y. T.; Di Tommaso, D.; Hogarthb, G.; Catlow, R. A. Dalton Trans. 2011, 40, 402
85. Chen, H-Y. T.; Di Tommaso, D.; Hogarthb, G.; Catlow, R. A. Dalton Trans. 2012, 41, 1867
86. 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
87. O, W. W. N.; Lough, A. J.; Morris, R. H. Chem. Commun. 2010, 46, 8240
88. O, W. W. N.; Morris, R. H. ACS Catal. 2013, 3, 32
89. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101
90. Grimme, S. J. Comput. Chem. 2006, 27, 1787
91. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865
92. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664
93. Becke, A. D. J. Chem. Phys. 1993, 98, 1372
94. Averkiev, B. B.; Truhlar, D. G. Catal. Sci. Technol. 2011, 1, 1526
95. Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2009, 5, 324
96. Zhao, Y.; Truhlar, D. G. Chem. Phys. Lett. 2011, 502, 1
97. Dang, L.; Yang, X.; Zhou, J.; Brothers, E. N.; Hall, M. B. J. Phys. Chem. A 2012, 116, 476
98. Romero, P. E.; Whited, M. T.; Grubbs, R. H. Organometallics 2008, 27, 3422
99. Kloek, S. M.; Heinekey, D. M.; Goldberg, K. I. Organometallics 2006, 25, 3007
100. Findlater, M.; Bernskoetter, W. H.; Brookhart, M. J. Am. Chem. Soc. 2010, 132, 4534
101. Abdur-Rashid, K.; Fatz, M.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2001, 123, 7473
102. Abdur-Rashid, K.; Clapham, S. E.; Hadzovic, A.; Harvey, J. N.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2002, 124, 15104
103. Zimmer-De Iuliis, M.; Morris, R. H. J. Am. Chem. Soc. 2009, 131, 11263
104. Hadzovic, A.; Song, D.; MacLaughlin, C. M.; Morris, R. H. Organometallics 2007, 26, 5987
105. Hasanayn, F.; Morris, R. H. Inorg. Chem. 2012, 51, 10808
106. Haynes, A.; Meijer, A. J. H. M.; Lyons, J. R.; Adams, H. Inorg. Chem. 2009, 48, 28
107. Hasanayn, F.; Abu-El-Ez, D. Inorg. Chem. 2010, 49, 9162
108. Hasanayn, F.; Achord, P.; Braunstein, P.; Magnier, H. J; Krogh-Jespersen, K.; Goldman, A. S. Organometallics 2012, 31, 4680
109. Fan, L.; Krzywicki, A.; Somogyvari, A.; Ziegler, T. Inorg. Chem. 1996, 35, 4003
110. Deng, L.; Woo, T. K.; Cavallo, L.; Margl, P. M.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 6177
111. Svensson, M.; Matsubara, T.; Morokuma, K. Organometallics 1996, 15, 5568
112. Froese, R. D. J.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 1581
113. Ferreira, D. A. C.; Meneghetti, S. M. P.; de Oliveira Neto, M.; Rocha, W. R.; Meneghetti, M. R. J. Braz. Chem. Soc. 2011, 22, 428
114. Strömberg, S.; Zetterberg, K.; Siegbahn, P. E. M. Dalton Trans. 1997, 4147
115. Heyndrickx, W.; Occhipinti, G.; Minenkov, Y.; Jensen, V. R. Chem. Eur. J. 2011, 17, 14628
116. Kuniyasu, H.; Sanagawa, A.; Nakane, D.; Iwasaki, T.; Kambe, N.; Bobuatong, K.; Lu, Y.; Ehara, M. Organometallics 2013, 32, 2026
117. Gnanaprakasam, B.; Ben-David, Y.; Milstein, D. Adv. Synth. Catal. 2010, 352, 3169
118. Blum, O.; Milstein, D. J. Organomet. Chem. 2000, 593-594, 479
119. Smythe, N. A.; Grice, K. A.; Williams, B. S.; Goldberg, K. I. Organometallics 2009, 28, 277
120. Fafard, C. M.; Ozerov, O. V. Inorg. Chim. Acta 2007, 360, 286
121. Baratta, W.; Siega, K.; Rigo, P. Chem. Eur. J. 2007, 13, 7479
122. Prokopchuk, D. E.; Morris, R. H. Organometallics 2012, 31, 7375
123. Zell, T.; Butschke, B.; Ben-David, Y.; Milstein, D. Chem. Eur. J. 2013, 19, 8068
124. Spasyuk, D.; Smith, S.; Gusev, D. G. Angew. Chem., Int. Ed. 2013, 52, 2538
125. Runyu, H.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135
126. Krug, C.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 1674
127. Krug, C.; Hartwig, J. F. Organometallics 2004, 23, 4594
128. Darensbourg, D. J.; Sanchez, K. M.; Rheingold, A. L. J. Am. Chem. Soc. 1987, 109, 290
129. Arunachalampillai, A.; Loganathan, N.; Wendt, O. F. Polyhedron 2012, 32, 24
130. Handgraaf, J.-W.; Meijer, E. J. J. Am. Chem. Soc. 2007, 129, 3099
131. Dub, P. A.; Ikariya, T. J. Am. Chem. Soc. 2013, 135, 2605
132. Sandoval, C. A.; Ohkuma, T.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490
133. Casey, C. P.; Johnson, J. B.; Singer, S. W.; Cui, Q. J. Am. Chem. Soc. 2005, 127, 3100
134. Hedberg, C.; Kallstrom, K.; Arvidsson, P. I.; Brandt, P.; Andersson, P. G. J. Am. Chem. Soc. 2005, 127, 15083
135. Xin Zhang, X.; Guo, X.; Chen, Y.; Tang, Y.; Lei, M.; Fang, W. Phys. Chem. Chem. Phys. 2012, 14, 6003
136. Montag, M.; Zhang, J.; Milstein, D. J. Am. Chem. Soc. 2012, 134, 10325
137. Huff, C. A.; Kampf, J. W.; Sanford, M. S. Organometallics 2012, 31, 4643
138. Huff, C. A.; Kampf, J. W.; Sanford, M. S. Chem. Commun. 2013, 49, 7147
139. Milstein, D. Top. Catal. 2010, 53, 915
140. Gunanathan, C.; Milstein, D. Top. Organomet. Chem. 2011, 37, 55
141. Poverenove, E.; Milstein, D. Top. Organomet. Chem. 2013, 40, 21
142. Vogt, M.; Gargir, M.; Iron, M. A.; Diskin-Posner, Y.; Ben-David, Y.; Milstein, D. Chem. Eur. J. 2012, 18, 9194
143. Langer, R.; Iron, M. A.; Konstantinovski, L.; Diskin-Posner, Y.; Leitus, G.; Ben-David, Y.; Milstein, D. Chem. Eur. J. 2012, 18, 7196
144. Balaraman, E.; Khaskin, E.; Leitus, G.; Milstein, D. Nat. Chem. 2013, 5, 122
145. Zeng, G.; Li, S. Inorg. Chem. 2011, 50, 10572