Computational mechanistic studies on reactions of transition metal complexes with noninnocent pincer ligands: Aromatization-dearomatization or not

ACS Catalysis

Volumn 5, Issue 3, 2015, Pages 1895-1913

  Li, Haixia ^a   Hall, Michael B ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

acridine based ligands; aromatization dearomatization; catalysis; dehydrogenative coupling reactions; DFT calculations; hydrogenation reactions; mechanistic studies; pyridine based ligands; transition metal complexes with noninnocent pincer ligands; bond activation

Indexed keywords

AROMATIZATION; CATALYSIS; CHEMICAL ACTIVATION; CHEMICAL BONDS; CHEMICAL REACTIONS; DESIGN FOR TESTABILITY; HYDROGENATION; MECHANICS; METAL COMPLEXES; METALS; NUMERICAL METHODS; PYRIDINE; SYNTHESIS (CHEMICAL); TRANSITION METAL COMPOUNDS; TRANSITION METALS;

BOND ACTIVATION; DEAROMATIZATION; DEHYDROGENATIVE COUPLING; DFT CALCULATION; HYDROGENATION REACTIONS; MECHANISTIC STUDIES; PINCER LIGANDS;

LIGANDS;

EID: 84924257821     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs501875z     Document Type: Review

References (97)

1. Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; WILEY-VCH Verlag GmbH and Co. KGaA: Weinheim, 2004, Vol. 1, pp 1-631.
2. Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord. Chem. Rev. 2004, 248, 2201-2237 10.1016/j.ccr.2004.04.007
3. Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300-1308 10.1021/ar700134q
4. Grützmacher, H. Angew. Chem., Int. Ed. 2008, 47, 1814-1818 10.1002/anie.200704654
5. Lyaskovskyy, V.; de Bruin, B. ACS Catal. 2012, 2, 270-279 10.1021/cs200660v
6. van der Vlugt, J. I. Eur. J. Inorg. Chem. 2012, 363-375 10.1002/ejic.201100752
7. Milstein, D. Top. Catal. 2010, 53, 915-923 10.1007/s11244-010-9523-7
8. Gunanathan, C.; Milstein, D. Acc. Chem. Res. 2011, 44, 588-602 10.1021/ar2000265
9. Gunanathan, C.; Milstein, D. Science 2013, 341, 1229712 10.1126/science.1229712
10. Gunanathan, C.; Milstein, D. Chem. Rev. 2014, 114, 12024-12087 10.1021/cr5002782
11. Reguillo, R.; Grellier, M.; Vautravers, N.; Vendier, L.; Sabo-Etienne, S. J. Am. Chem. Soc. 2010, 132, 7854-7855 10.1021/ja102759z
12. Song, C.; Qu, S.; Tao, Y.; Dang, Y.; Wang, Z.-X. ACS. Catal. 2014, 4, 2854-2865 10.1021/cs5008156
13. Friedrich, A.; Drees, M.; auf der Günne, J. S.; Schneider, S. J. Am. Chem. Soc. 2009, 131, 17552-17553 10.1021/ja908644n
14. Friedrich, A.; Drees, M.; Käss, M.; Herdtweck, E.; Schneider, S. Inorg. Chem. 2010, 49, 5482-5494 10.1021/ic100358m
15. Yang, X. ACS. Catal. 2013, 3, 2684-2688 10.1021/cs400862x
16. Yang, X. ACS. Catal. 2014, 4, 1129-1133 10.1021/cs500061u
17. Hehre, W. J.; Ditchfie, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261 10.1063/1.1677527
18. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; Defrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654-3665 10.1063/1.444267
19. Andrae, D.; Häussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chem. Acc. 1990, 77, 123-141 10.1007/BF01114537
20. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101 10.1063/1.2370993
21. Tao, J. M.; Perdew, J. P.; Staroverov, V. N.; Scuseria, G. E. Phys. Rev. Lett. 2003, 91, 146401 10.1103/PhysRevLett.91.146401
22. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104 10.1063/1.3382344
23. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789 10.1103/PhysRevB.37.785
24. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206 10.1016/0009-2614(89)87234-3
25. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652 10.1063/1.464913
26. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241 10.1007/s00214-007-0310-x
27. Chai, J.-D.; Head-Gordon, M. Phys. Chem. Chem. Phys. 2008, 10, 6615-6620 10.1039/b810189b
28. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639-5648 10.1063/1.438980
29. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654 10.1063/1.438955
30. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294-301 10.1002/jcc.540040303
31. Dunning, T. H. J. Chem. Phys. 1989, 90, 1007-1023 10.1063/1.456153
32. Feller, D. J. Comput. Chem. 1996, 17, 1571-1586 10.1002/jcc.9
33. Schuchardt, K. L.; Didier, B. T.; Elsethagen, T.; Sun, L.; Gurumoorthi, V.; Chase, J.; Li, J.; Windus, T. L. J. Chem. Inf. Model. 2007, 47, 1045-1052 10.1021/ci600510j
34. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865-3868 10.1103/PhysRevLett.77.3865
35. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1997, 78, 1396-1396 10.1103/PhysRevLett.78.1396
36. Perdew, J. P.; Emzerhof, M.; Burke, K. J. Chem. Phys. 1996, 105, 9982-9985 10.1063/1.472933
37. Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158-6170 10.1063/1.478522
38. Peverati, R.; Truhlar, D. G. J. Chem. Phys. 2011, 135, 191102 10.1063/1.3663871
39. Boese, A. D.; Martin, J. M. L. J. Chem. Phys. 2004, 121, 3405-3416 10.1063/1.1774975
40. Yanai, T.; Tew, D. P.; Handy, N. C. Chem. Phys. Lett. 2004, 393, 51-57 10.1016/j.cplett.2004.06.011
41. Chai, J.-D.; Head-Gordon, M. J. Chem. Phys. 2008, 128, 084106 10.1063/1.2834918
42. Peverati, R.; Truhlar, D. G. Phys. Chem. Chem. Phys. 2012, 14, 16187-16191 10.1039/c2cp42576a
43. Henderson, T. M.; Izmaylov, A. F.; Scuseria, G. E.; Savin, A. J. Chem. Theory Comput. 2008, 4, 1254-1262 10.1021/ct800149y
44. Heyd, J.; Scuseria, G. E. J. Chem. Phys. 2004, 121, 1187-1192 10.1063/1.1760074
45. Heyd, J.; Scuseria, G. E. J. Chem. Phys. 2004, 120, 7274-7280 10.1063/1.1668634
46. Vydrov, O. A.; Scuseria, G. E. J. Chem. Phys. 2006, 125, 234109 10.1063/1.2409292
47. Purvis, G. D., III; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918 10.1063/1.443164
48. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968-5975 10.1063/1.453520
49. Fukui, K. Acc. Chem. Res. 1981, 14, 363-368 10.1021/ar00072a001
50. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396 10.1021/jp810292n
51. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, 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.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; 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, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision B.01; Gaussian, Inc.: Wallingford CT, 2009.
52. Werner, H.-J.; Knowles, P. J.; Knizia, G.; Manby, F. R.; Schütz, M. WIREs Comput. Mol. Sci. 2012, 2, 242-253 10.1002/wcms.82
53. Werner, H.-J.; Knowles, P. J.; Knizia, G.; Manby, F. R.; Schütz, M.; Celani, P.; Korona, T.; Lindh, R.; Mitrushenkov, A.; Rauhut, G.; Shamasundar, K. R.; Adler, T. B.; Amos, R. D.; Bernhardsson, A.; Berning, A.; Cooper, D. L.; Deegan, M. J. O.; Dobbyn, A. J.; Eckert, F.; Goll, E.; Hampel, C.; Hesselmann, A.; Hetzer, G.; Hrenar, T.; Jansen, G.; Köppl, C.; Liu, Y.; Lloyd, A. W.; Mata, R. A.; May, A. J.; McNicholas, S. J.; Meyer, W.; Mura, M. E.; Nicklass, A.; ONeill, D. P.; Palmieri, P.; Peng, D.; Pflüger, K.; Pitzer, R.; Reiher, M.; Shiozaki, T.; Stoll, H.; Stone, A. J.; Tarroni, R.; Thorsteinsson, T.; Wang, M. MOLPRO, version 2012.1, a package of ab initio programs; see http://www.molpro.net.
54. Li, H.; Wang, Z. Sci. Chin. Chem. 2012, 55, 1991-2008 10.1007/s11426-012-4713-8
55. Zeng, G.; Guo, Y.; Li, S. Inorg. Chem. 2009, 48, 10257-10263 10.1021/ic9013587
56. Iron, M. A.; Ben-Ari, E.; Cohen, R.; Milstein, D. Dalton Trans. 2009, 9433-9439 10.1039/b909852f
57. Schwartsburd, L.; Iron, M. A.; Konstantinovski, L.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Milstein, D. Organometallics 2010, 29, 3817-3827 10.1021/om1004435
58. Li, J.; Shiota, Y.; Yoshizawa, K. J. Am. Chem. Soc. 2009, 131, 13584-13585 10.1021/ja905073s
59. Yang, X.; Hall, M. B. J. Am. Chem. Soc. 2010, 132, 120-130 10.1021/ja9041065
60. Sandhya, K. S.; Suresh, C. H. Organometallics 2011, 30, 3888-3891 10.1021/om200046u
61. Khaskin, E.; Iron, M. A.; Shimon, L. J. W.; Zhang, J.; Milstein, D. J. Am. Chem. Soc. 2010, 132, 8542-8543 10.1021/ja103130u
62. Anaby, A.; Butschke, B.; Ben-David, Y.; Shimon, L. J. W.; Leitus, G.; Feller, M.; Milstein, D. Organometallics 2014, 33, 3716-3726 10.1021/om500311a
63. Li, H.; Wang, X.; Huang, F.; Lu, G.; Jiang, J.; Wang, Z.-X. Organometallics 2011, 30, 5233-5247 10.1021/om200620n
64. Cho, D.; Ko, K. C.; Lee, J. Y. Organometallics 2013, 32, 4571-4576 10.1021/om4005324
65. Zeng, G.; Li, S. Inorg. Chem. 2011, 50, 10572-10580 10.1021/ic200205e
66. Li, H.; Wang, X.; Wen, M.; Wang, Z.-X. Eur. J. Inorg. Chem. 2012, 5011-5020 10.1002/ejic.201200473
67. Sandhya, K. S.; Suresh, C. H. Organometallics 2013, 32, 2926-2933 10.1021/om4001428
68. Li, H.; Hall, M. B. J. Am. Chem. Soc. 2014, 136, 383-395 10.1021/ja410541v
69. Qu, S.; Dang, Y.; Song, C.; Wen, M.; Huang, K.-W.; Wang, Z.-X. J. Am. Chem. Soc. 2014, 136, 4974-4991 10.1021/ja411568a
70. Yang, X. Inorg. Chem. 2011, 50, 12836-12843 10.1021/ic2020176
71. Cantillo, D. Eur. J. Inorg. Chem. 2011, 3008-3013 10.1002/ejic.201100443
72. Li, H.; Wen, M.; Wang, Z.-X. Inorg. Chem. 2012, 51, 5716-5727 10.1021/ic300175b
73. Yang, X. ACS Catal. 2012, 2, 964-970 10.1021/cs3000683
74. Hasanayn, F.; Baroudi, A.; Bengali, A. A.; Goldman, A. S. Organometallics 2013, 32, 6969-6985 10.1021/om4005127
75. Hasanayn, F.; Baroudi, A. Organometallics 2013, 32, 2493-2496 10.1021/om400122n
76. Hasanayn, F.; Harb, H. Inorg. Chem. 2014, 53, 8334-8349 10.1021/ic500743u
77. Yang, X. ACS Catal. 2011, 1, 849-854 10.1021/cs2000329
78. Ye, X.; Plessow, P. N.; Brinks, M. K.; Schelwies, M.; Schaub, T.; Rominger, F.; Paciello, R.; Limbach, M.; Hofmann, P. J. Am. Chem. Soc. 2014, 136, 5923-5929 10.1021/ja409368a
79. Ben-Ari, E.; Leitus, G.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2006, 128, 15390-15391 10.1021/ja066411i
80. Kohl, S. W.; Weiner, L.; Schwartsburd, L.; Konstantinovski, L.; Shimon, L. J. W.; Ben-David, Y.; Iron, M. A.; Milstein, D. Science 2009, 324, 74-77 10.1126/science.1168600
81. Chen, Y.; Fang, W.-H. J. Phys. Chem. A 2010, 114, 10334-10338 10.1021/jp1065105
82. Hermans, J.; Wang, L. J. Am. Chem. Soc. 1997, 119, 2707-2714 10.1021/ja963568+
83. Strajbl, M.; Sham, Y. Y.; Villa, J.; Chu, Z. T.; Warshel, A. J. Phys. Chem. B 2000, 104, 4578-4584 10.1021/jp0003095
84. Gunanathan, C.; Ben-David, Y.; Milstein, D. Science 2007, 317, 790-792 10.1126/science.1145295
85. Montag, M.; Zhang, J.; Milstein, D. J. Am. Chem. Soc. 2012, 134, 10325-10328 10.1021/ja303121v
86. Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 2005, 127, 10840-10841 10.1021/ja052862b
87. Gnanaprakasam, B.; Zhang, J.; Milstein, D. Angew. Chem., Int. Ed. 2010, 49, 1468-1471 10.1002/anie.200907018
88. Balaraman, E.; Khaskin, E.; Leitus, G.; Milstein, D. Nat. Chem. 2013, 5, 122-125 10.1038/nchem.1536
89. Srimani, D.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2013, 52, 4012-4015 10.1002/anie.201300574
90. Langer, R.; Leitus, G.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50, 2120-2124 10.1002/anie.201007406
91. Balaraman, E.; Gnanaprakasam, B.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2010, 132, 16756-16758 10.1021/ja1080019
92. Balaraman, E.; Gunanathan, C.; Zhang, J.; Shimon, L. J. W.; Milstein, D. Nat. Chem. 2011, 3, 609-614 10.1038/nchem.1089
93. Langer, R.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50, 9948-9952 10.1002/anie.201104542
94. Vogt, M.; Gargir, M.; Iron, M. A.; Diskin-Posner, Y.; Ben-David, Y.; Milstein, D. Chem.-Eur. J. 2012, 18, 9194-9197 10.1002/chem.201201730
95. Gunanathan, C.; Milstein, D. Angew. Chem., Int. Ed. 2008, 47, 8661-8664 10.1002/anie.200803229
96. Gunanathan, C.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2009, 131, 3146-3147 10.1021/ja808893g
97. Gunanathan, C.; Gnanaprakasam, B.; Iron, M. A.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2010, 132, 14763-14765 10.1021/ja107770y