Dehydrogenation of formic acid by Ir-bisMETAMORPhos complexes: Experimental and computational insight into the role of a cooperative ligand

Chemical Science

Volumn 6, Issue 2, 2015, Pages 1027-1034

  Oldenhof, Sander ^a   Lutz, Martin ^b   De Bruin, Bas ^a   Van Der Vlugt, Jarl Ivar ^a   Reek, Joost N H ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATION; COORDINATION REACTIONS; DEHYDROGENATION; FORMIC ACID; HYDROGEN BONDS; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

BASE-FREE; COORDINATION SPHERE; DEHYDROGENATION REACTIONS; DFT CALCULATION; DUAL ROLE; OXIDATIVE ADDITIONS; TRANSITION STATE; TURNOVER FREQUENCY;

IRIDIUM;

EID: 84921668380     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c4sc02555e     Document Type: Article

References (70)

1. (a) M. Raynal, P. Ballester, A. Vidal-Ferran and P. W. N. M. van Leeuwen, Chem. Soc. Rev., 2014, 43, 1734-1787;
2. (b) M. Raynal, P. Ballester, A. Vidal-Ferran and P. W. N. M. van Leeuwen, Chem. Soc. Rev., 2014, 43, 1660-1733;
3. (c) T. S. Koblenz, J. Wassenaar and J. N. H. Reek, Chem. Soc. Rev., 2008, 37, 247-262.
4. (a) B. Breit and W. Seiche, J. Am. Chem. Soc., 2003, 125, 6608-6609;
5. (b) S. Zhu, J. V. Ruppel, H. Lu, L. Wojtas and X. P. Zhang, J. Am. Chem. Soc., 2008, 130, 5042-5043;
6. (c) J. Meeuwissen, M. Kuil, A. M. van der Burg, A. J. Sandee and J. N. H. Reek, Chem.-Eur. J., 2009, 15, 10272-10279;
7. (d) L. Diab, T. Šmejkal, J. Geier and B. Breit, Angew. Chem., Int. Ed., 2009, 48, 8022-8026;
8. J. Meeuwissen and J. N. H. Reek, Nat. Chem., 2010, 2, 615-621;
9. (f) A. J. Sandee and J. N. H. Reek, Dalton Trans., 2006, 3385-3391;
10. (g) S. Carboni, C. Gennari, L. Pignataro and U. Piarulli, Dalton Trans., 2011, 40, 4355-4373.
11. (a) S. Das, C. D. Incarvito, R. H. Crabtree and G. W. Brudvig, Science, 2006, 312, 1941-1943;
12. (b) L. Du, P. Cao, J. Xing, Y. Lou, L. Jiang, L. Li and J. Liao, Angew. Chem., Int. Ed., 2013, 52, 4207-4211;
13. (c) P. Dydio and J. N. H. Reek, Chem. Sci., 2014, 5, 2135-2145;
14. (d) D. B. Grotjahn, Chem.-Eur. J., 2005, 11, 7146-7153;
15. (e) T. Šmejkal and B. Breit, Angew. Chem., Int. Ed., 2008, 47, 311-315;
16. (f) P.-A. R. Breuil, F. W. Patureau and J. N. H. Reek, Angew. Chem., Int. Ed., 2009, 48, 2162-2165;
17. (g) P. Dydio, W. I. Dzik, M. Lutz, B. de Bruin and J. N. H. Reek, Angew. Chem., 2011, 123, 416-420;
18. (h) P. Dydio, C. Rubay, T. Gadzikwa, M. Lutz and J. N. H. Reek, J. Am. Chem. Soc., 2011, 133, 17176-17179;
19. (i) P. Dydio and J. N. H. Reek, Angew. Chem., Int. Ed., 2013, 52, 3878-3882;
20. (j) Y. Gumrukcu, B. de Bruin and J. N. H. Reek, ChemSusChem, 2014, 7, 890-896;
21. (k) W. I. Dzik, X. Xu, X. P. Zhang, J. N. H. Reek and B. de Bruin, J. Am. Chem. Soc., 2010, 132, 10891-10902;
22. (l) V. Lyaskovskyy, A. I. O. Suarez, H. Lu, H. Jiang, X. P. Zhang and B. de Bruin, J. Am. Chem. Soc., 2011, 133, 12264-12273;
23. (m) A. I. O. Suarez, H. Jiang, X. P. Zhang and B. de Bruin, Dalton Trans., 2011, 40, 5697-5705;
24. (n) Y. Chen, K. B. Fields and X. P. Zhang, J. Am. Chem. Soc., 2004, 126, 14718-14719.
25. (a) F. W. Patureau, M. Kuil, A. J. Sandee and J. N. H. Reek, Angew. Chem., Int. Ed., 2008, 47, 3180-3183;
26. (b) F. W. Patureau, S. de Boer, M. Kuil, J. Meeuwissen, P.-A. R. Breuil, M. A. Siegler, A. L. Spek, A. J. Sandee, B. de Bruin and J. N. H. Reek, J. Am. Chem. Soc., 2009, 131, 6683-6685;
27. (c) T. León, M. Parera, A. Roglans, A. Riera and X. Verdaguer, Angew. Chem., Int. Ed., 2012, 51, 6951-6955;
28. (d) F. W. Patureau, M. A. Siegler, A. L. Spek, A. J. Sandee, S. Jugé, S. Aziz, A. Berkessel and J. N. H. Reek, Eur. J. Inorg. Chem., 2012, 496-503;
29. (e) F. G. Terrade, M. Lutz, J. I. van der Vlugt and J. N. H. Reek, Eur. J. Inorg. Chem., 2014, 1826-1835;
30. (f) S. Oldenhof, B. de Bruin, M. Lutz, M. A. Siegler, F. W. Patureau, J. I. van der Vlugt and J. N. H. Reek, Chem.-Eur. J., 2013, 19, 11507-11511.
31. (a) R. Hille, Chem. Rev., 1996, 96, 2757-2816;
32. (b) C. M. P. T. Reda, N. J. Abram and J. Hirst, Proc. Natl. Acad. Sci. U. S. A., 2008, 105, 10654-10658;
33. (c) M. J. Romao, Dalton Trans., 2009, 4053-4068;
34. (d) C. Mota, M. Rivas, C. Brondino, I. Moura, J. G. Moura, P. González and N. F. S. A. Cerqueira, J. Biol. Inorg. Chem., 2011, 16, 1255-1268;
35. (e) M. Tiberti, E. Papaleo, N. Russo, L. De Gioia and G. Zampella, Inorg. Chem., 2012, 51, 8331-8339;
36. (f) K. Schuchmann and V. Müller, Science, 2013, 342, 1382-1385.
37. (a) A. Boddien, D. Mellmann, F. Gärtner, R. Jackstell, H. Junge, P. J. Dyson, G. Laurenczy, R. Ludwig and M. Beller, Science, 2011, 333, 1733-1736;
38. (b) J. F. Hull, Y. Himeda, W.-H. Wang, B. Hashiguchi, R. Periana, D. J. Szalda, J. T. Muckerman and E. Fujita, Nat. Chem., 2012, 4, 383-388;
39. (c) T. Zell, B. Butschke, Y. Ben-David and D. Milstein, Chem.-Eur. J., 2013, 19, 8068-8072;
40. (d) E. A. Bielinski, P. O. Lagaditis, Y. Zhang, B. Q. Mercado, C. Würtele, W. H. Bernskoetter, N. Hazari and S. Schneider, J. Am. Chem. Soc., 2014, 136, 10234-10237;
41. (e) Y. Manaka, W.-H. Wang, Y. Suna, H. Kambayashi, J. T. Muckerman, E. Fujita and Y. Himeda, Catal. Sci. Technol., 2014, 4, 34-37;
42. (f) W.-H. Wang, S. Xu, Y. Manaka, Y. Suna, H. Kambayashi, J. T. Muckerman, E. Fujita and Y. Himeda, ChemSusChem, 2014, 7, 1976-1983.
43. (a) S. Kuwata and T. Ikariya, Chem.-Eur. J., 2011, 17, 3542-3556;
44. (b) S. Schneider, J. Meiners and B. Askevold, Eur. J. Inorg. Chem., 2012, 412-429;
45. (c) J. I. van der Vlugt, Eur. J. Inorg. Chem., 2012, 363-375;
46. (d) B. Zhao, Z. Han and K. Ding, Angew. Chem., Int. Ed., 2013, 52, 4744-4788;
47. (e) G. A. Filonenko, M. P. Conley, C. Copéret, M. Lutz, E. J. M. Hensen and E. A. Pidko, ACS Catal., 2013, 3, 2522-2526;
48. (f) D. V. Gutsulyak, W. E. Piers, J. Borau-Garcia and M. Parvez, J. Am. Chem. Soc., 2013, 135, 11776-11779;
49. (g) C. M. Moore and N. K. Szymczak, Chem. Commun., 2013, 49, 400-402;
50. (h) G. Zhang, K. V. Vasudevan, B. L. Scott and S. K. Hanson, J. Am. Chem. Soc., 2013, 135, 8668-8681.
51. (a) G. A. Filonenko, E. J. M. Hensen and E. A. Pidko, Catal. Sci. Technol., 2014, 4(10), 3474-3485;
52. (b) T. J. Schmeier, G. E. Dobereiner, R. H. Crabtree and N. Hazari, J. Am. Chem. Soc., 2011, 133, 9274-9277;
53. (c) T. W. Myers and L. A. Berben, Chem. Sci., 2014, 5, 2771-2777.
54. (a) T. Koike and T. Ikariya, Adv. Synth. Catal., 2004, 346, 37-41;
55. (b) P. Š. J. Václavík, B. Vilhanová, J. Pecháček, M. Kuzma and P. Kačer, Molecules, 2013, 18, 6804-6828;
56. (c) A. Nova, D. J. Taylor, A. J. Blacker, S. B. Duckett, R. N. Perutz and O. Eisenstein, Organometallics, 2014, 33, 3433-3442.
57. (a) R. Sánchez-de-Armas, L. Xue and M. S. G. Ahlquist, Chem.-Eur. J., 2013, 19, 11869-11873;
58. (b) X. Yang, Dalton Trans., 2013, 42, 11987-11991.
59. (a) H. Bauer, U. Nagel and W. Beck, J. Organomet. Chem., 1985, 290, 219-229;
60. (b) M. Feller, A. Karton, G. Leitus, J. M. L. Martin and D. Milstein, J. Am. Chem. Soc., 2006, 128, 12400-12401;
61. (c) J. J. Adams, A. Lau, N. Arulsamy and D. M. Roddick, Organometallics, 2011, 30, 689-696.
62. (a) C. Yin, Z. Xu, S.-Y. Yang, S. M. Ng, K. Y. Wong, Z. Lin and C. P. Lau, Organometallics, 2001, 20, 1216-1222;
63. (b) M. S. G. Ahlquist, J. Mol. Catal. A: Chem., 2010, 324, 3-8;
64. (c) X. Yang, ACS Catal., 2011, 1, 849-854;
65. (d) R. Tanaka, M. Yamashita, L. W. Chung, K. Morokuma and K. Nozaki, Organometallics, 2011, 30, 6742-6750;
66. (e) A. Pavlova and E. J. Meijer, ChemPhysChem, 2012, 13, 3492-3496.
67. T. J. Schmeier, G. E. Dobereiner, R. H. Crabtree and N. Hazari, J. Am. Chem. Soc., 2011, 133, 9274-9277.
68. A. J. C. Walters, J. N. H. Reek and B. de Bruin, ACS Catal., 2014, 4, 1376-1389.
69. (a) D. H. Wertz, J. Am. Chem. Soc., 1980, 102, 5316-5322;
70. (b) N. Schneider, M. Finger, C. Haferkemper, S. Bellemin-Laponnaz, P. Hofmann and L. Gade, Angew. Chem., Int. Ed., 2009, 48, 1609-1613.