Characterization of porphyrin-Co(III)-'nitrene radical' species relevant in catalytic nitrene transfer reactions

Journal of the American Chemical Society

Volumn 137, Issue 16, 2015, Pages 5468-5479

  Goswami, Monalisa ^a   Lyaskovskyy, Volodymyr ^a   Domingos, Sérgio R ^b   Buma, Wybren Jan ^b   Woutersen, Sander ^b   Troeppner, Oliver ^c   Ivanović Burmazović, Ivana ^c   Lu, Hongjian ^d   Cui, Xin ^d   Zhang, X Peter ^d   Reijerse, Edward J ^e   Debeer, Serena ^e   Van Schooneveld, Matti M ^e   Pfaff, Florian Felix ^f   Ray, Kallol ^f   De Bruin, Bas ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

^c UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^d UNIVERSITY OF SOUTH FLORIDA   (United States)

^e MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

^f HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRON TRANSITIONS; FREE RADICAL REACTIONS; LIGANDS; PORPHYRINS; REACTION INTERMEDIATES; SPECTROSCOPIC ANALYSIS; STYRENE;

COBALT PORPHYRINS; ONE-ELECTRON TRANSFER; RADICAL COMPLEXES; SINGLE ELECTRON TRANSFER; SPECTROSCOPIC STUDIES; TETRAPHENYLPORPHYRINS; TRANSFER REACTION; UNPAIRED ELECTRONS;

COBALT COMPOUNDS;

COBALT COMPLEX; NITRENE; NITROGEN DERIVATIVE; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG; COBALT; IMINE; LIGAND; METALLOPORPHYRIN; PHENYLNITRENE;

AMINATION; ARTICLE; AZIRIDINATION; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; ELECTROSPRAY MASS SPECTROMETRY; HYDROGEN BOND; ULTRAVIOLET SPECTROSCOPY; X RAY ABSORPTION SPECTROSCOPY; CHEMISTRY; MOLECULAR MODEL; OXIDATION REDUCTION REACTION; SPECTROSCOPY;

CATALYSIS; COBALT; IMINES; LIGANDS; METALLOPORPHYRINS; MODELS, MOLECULAR; OXIDATION-REDUCTION; SPECTRUM ANALYSIS;

EID: 84928731099     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b01197     Document Type: Article

References (83)

1. Godula, K.; Sames, D. Science 2006, 312, 67-72
2. Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507-514
3. Shilov, A. E.; Shul, G. B. Chem. Rev. 1997, 97, 2879-2932
4. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911-935
5. Lu, H.-J.; Zhang, X. P. Chem. Soc. Rev. 2011, 40, 1899-1909
6. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417-424
7. Davies, H. M. L. Angew. Chem., Int. Ed. 2006, 45, 6422-6425
8. Hili, R.; Yudin, A. K. Nat. Chem. Biol. 2006, 2, 284-287
9. Suarez, A. I. O.; Jiang, H.; Zhang, X. P.; de Bruin, B. Dalton Trans. 2011, 40, 5697-5705
10. Jin, L.-M.; Xu, X.; Lu, H.; Cui, X.; Wojtas, L.; Zhang, X. P. Angew. Chem., Int. Ed. 2013, 52, 5309-5313
11. Lu, H.; Subbarayan, V.; Tao, J.; Zhang, X. P. Organometallics 2010, 29, 389-393
12. Lu, H.; Hu, Y.; Jiang, H.; Wojtas, L.; Zhang, X. P. Org. Lett. 2012, 14, 5158-5161
13. Jin, L.; Lu, H.; Cui, Y.; Lizardi, C. L.; Arzua, T. N.; Wojtas, L.; Cui, X.; Zhang, X. P. Chem. Sci. 2014, 5, 2422-2427
14. Catino, A. J.; Nichols, J. M.; Forslund, R. E.; Doyle, M. P. Org. Lett. 2005, 7, 2787-2790
15. Shen, M.; Leslie, B. E.; Driver, T. G. Angew. Chem., Int. Ed. 2008, 47, 5056-5059
16. Stokes, B. J.; Dong, H.; Leslie, B. E.; Pumphrey, A. L.; Driver, T. G. J. Am. Chem. Soc. 2007, 129, 7500-7501
17. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J.; V, S. U.; April, R. V.; H, C. J. Am. Chem. Soc. 2001, 123, 6935-6936
18. Shou, W. G.; Li, J.; Guo, T.; Lin, Z.; Jia, G. Organometallics 2009, 28, 6847-6854
19. Liang, J.; Yuan, S.; Huang, J.; Che, C.-M. J. Org. Chem. 2004, 69, 3610-3619
20. Fantauzzi, S.; Gallo, E.; Caselli, A.; Ragaini, F.; Casati, N.; Macchi, P.; Cenini, S. Chem. Commun. 2009, 3952-3954
21. Abu-Omar, M. M. Dalton Trans. 2011, 40, 3435-3444
22. Zhang, J.; Hong Chan, P. W.; Che, C.-M. Tetrahedron Lett. 2005, 46, 5403-5408
23. Albone, D. P.; Aujla, P. S.; Taylor, P. C. J. Org. Chem. 1998, 63, 9569-9571
24. Clark, J. S.; Roche, C. Chem. Commun. 2005, 5175-5177
25. Fructos, M. R.; Trofimenko, S.; Diaz-Requejo, M. M.; Perez, P. J. J. Am. Chem. Soc. 2006, 128, 11784-11791
26. Albone, D. P.; Challenger, S.; Derrick, A. M.; Fillery, S. M.; Irwin, J. L.; Parsons, C. M.; Takada, H.; Taylor, C.; Wilson, D. J. J. Org. Biomol. Chem. 2005, 107-111
27. Liu, Y.; Che, C.-M. Chem.-A Eur. J. 2010, 16, 10494-10501
28. Chen, Y.; Ruppel, J. V.; Zhang, X. P. J. Am. Chem. Soc. 2007, 129, 12074-12075
29. Zhu, S.; Xu, X.; Perman, J. A.; Zhang, X. P. J. Am. Chem. Soc. 2010, 132, 12796-12799
30. Zhu, S.; Ruppel, J. V.; Lu, H.; Wojtas, L.; Zhang, X. P. J. Am. Chem. Soc. 2008, 130, 5042-5043
31. Zhu, S.; Perman, J. a; Zhang, X. P. Angew. Chem., Int. Ed. Engl. 2008, 47, 8460-8463
32. Li, Z.; Capretto, D. A.; Rahaman, R.; He, C. Angew. Chem., Int. Ed. 2007, 46, 5184-5186
33. Chang, J. W. W.; Chan, P. W. H. Angew. Chem., Int. Ed. 2008, 47, 1138-1140
34. Yang, J.; Weinberg, R.; Breslow, R. Chem. Commun. 2000, 531-532
35. Chan, J.; Baucom, K. D.; Murry, J. A. J. Am. Chem. Soc. 2007, 129, 14106-14107
36. Liang, C.; Collet, F.; Robert-Peillard, F.; Müller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343-350
37. Driver, T. G. Org. Biomol.Chem. 2010, 8, 3831-3846
38. Intrieri, D.; Zardi, P.; Caselli, A.; Gallo, E. Chem. Commun. 2014, 50, 11440-11453
39. Jones, J. E.; Ruppel, J. V.; Gao, G.; Moore, T. M.; Zhang, X. P. J. Org. Chem. 2008, 73, 7260-7265
40. Gao, G.; Jones, J. E.; Vyas, R.; Harden, J. D.; Zhang, X. P. J. Org. Chem. 2006, 71, 6655-6658
41. Subbarayan, V.; Ruppel, J. V.; Zhu, S.; Perman, J. A.; Zhang, X. P. Chem. Commun. 2009, 4266-4268
42. Ruppel, J. V.; Jones, J. E.; Huff, C. A.; Kamble, R. M.; Chen, Y.; Zhang, X. P. Org. Lett. 2008, 10, 1995-1998
43. Lyaskovskyy, V.; Suarez, A. I. O.; Lu, H.; Jiang, H.; Zhang, X. P.; de Bruin, B. J. Am. Chem. Soc. 2011, 12264-12273
44. Luca, O. R.; Crabtree, R. H. Chem. Soc. Rev. 2013, 42, 1440-1459
45. Lyaskovskyy, V.; de Bruin, B. ACS Catal. 2012, 2, 270-279
46. Van der Vlugt, J. I. Eur. J. Inorg. Chem. 2012, 2012, 363-375
47. Pierpont, C. G.; Buchanan, R. M. Coord. Chem. Rev. 1981, 38, 45-87
48. Kaim, W.; Schwederski, B. Coord. Chem. Rev. 2010, 254, 1580-1588
49. Boyer, J. L.; Rochford, J.; Tsai, M.-K.; Muckerman, J. T.; Fujita, E. Coord. Chem. Rev. 2010, 254, 309-330
50. Lever, A. B. P. Coord. Chem. Rev. 2010, 254, 1397-1405
51. Jones, G. D.; Martin, J. L.; Mcfarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.; Brandon, R. J.; Konovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A. J. Am. Chem. Soc. 2006, 128, 13175-13183
52. Ciszewski, J. T.; Mikhaylov, D. Y.; Holin, K. V.; Kadirov, M. K.; Budnikova, Y. H.; Sinyashin, O.; Vicic, D. A. Inorg. Chem. 2011, 50, 8630-8635
53. Scarborough, C. C.; Lancaster, K. M.; DeBeer, S.; Weyhermüller, T.; Sproules, S.; Wieghardt, K. Inorg. Chem. 2012, 51, 3718-3732
54. Tejel, C.; Ciriano, M. A.; del Rio, M. P.; van den Bruele, F. J.; Hetterscheid, D. G. H.; Tsichlis i Spitas, N.; de Bruin, B. J. Am. Chem. Soc. 2008, 130, 5844-5845
55. Tejel, C.; Asensio, L.; del Río, M. P.; de Bruin, B.; López, J. A.; Ciriano, M. A. Angew. Chem., Int. Ed. 2011, 50, 8839-8843
56. Lu, C. C.; Bill, E.; Weyhermüller, T.; Bothe, E.; Wieghardt, K. J. Am. Chem. Soc. 2008, 130, 3181-3197
57. de Bruin, B.; Bill, E.; Bothe, E.; Weyhermüller, T.; Wieghardt, K. Inorg. Chem. 2000, 39, 2936-2947
58. Chirik, P. J.; Wieghardt, K. Science 2010, 327, 794-795
59. Tondreau, A. M.; Milsmann, C.; Patrick, A. D.; Hoyt, H. M.; Lobkovsky, E.; Wieghardt, K.; Chirik, P. J. J. Am. Chem. Soc. 2010, 132, 15046-15059
60. Intermolecular, I.; Russell, S. K.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2011, 133, 8858-8861
61. Bouwkamp, M. W.; Bowman, A. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 13340-13341
62. Dzik, W. I.; Zhang, X. P.; de Bruin, B. Inorg. Chem. 2011, 50, 9896-9903
63. Dzik, W. I.; Xu, X.; Zhang, X. P.; Reek, J. N. H.; de Bruin, B. J. Am. Chem. Soc. 2010, 132, 10891-10902
64. Lu, H.; Dzik, W. I.; Xu, X.; Wojtas, L.; de Bruin, B.; Zhang, X. P. J. Am. Chem. Soc. 2011, 133, 8518-8521
65. Suarez, A. I. O; Lyaskovskyy, V.; Reek, J. N. H.; van der Vlugt, J. I.; de Bruin, B. Angew. Chem., Int. Ed. 2013, 52, 12510-12529
66. Liu, Y.; Guan, X.; Wong, E. L.; Liu, P.; Huang, J.; Che, C. J. Am. Chem. Soc. 2013, 135, 7194-7204
67. Kundu, S.; Miceli, E.; Farquhar, E.; Pfaff, F. F.; Kuhlmann, U.; Hildebrandt, P.; Braun, B.; Greco, C.; Ray, K. J. Am. Chem. Soc. 2012, 134, 14710-14713
68. Lu, H.; Tao, J.; Jones, J. E.; Wojtas, L.; Zhang, X. P. Org. Lett. 2010, 12, 1248-1251
69. Au, S.; Huang, J.; Yu, W.; Fung, W.; Che, C.-M. J. Am. Chem. Soc. 1999, 121, 9120-9132
70. Leung, S. K.; Tsui, W.; Huang, J.; Che, C.; Liang, J.; Zhu, N. J. Am. Chem. Soc. 2005, 127, 16629-16640
71. Guo, Z.; Guan, X.; Huang, J.-S.; Tsui, W.-M.; Lin, Z.; Che, C.-M. Chem.-Eur. J. 2013, 19, 11320-11331
72. Law, S.-M.; Chen, D.; Chan, S. L.-F.; Guan, X.; Tsui, W.-M.; Huang, J.-S.; Zhu, N.; Che, C.-M. Chem.-Eur. J. 2014, 20, 11035-11047
73. Manca, G.; Gallo, E.; Intrieri, D.; Mealli, C. ACS Catal. 2014, 4, 823-832
74. See for example: Nam, W. Acc. Chem. Res. 2007, 40, 522-531 and references therein
75. The quartet-doublet gap might be underestimated, as hybrid functionals often overestimate the stability of higher-spin states: Swart, M. J. Chem. Theory Comput. 2008, 4, 2057-2066
76. Campo Dall' Orto, V.; Carballo, R.; Hurst, J. A.; Rezzano, I. Spectrochim. Acta, Part A 2005, 61, 2089-2093
77. Mu, X. H.; Kadish, K. M. Inorg. Chem. 1989, 28, 3743-3747
78. Lin, X. Q.; Kadish, K. M. Inorg. Chem. 1986, 25, 3242-3248
79. Dey, S.; Ikbal, S. A.; Rath, S. P. New J. Chem. 2014, 38, 1458-1470
80. Gasyna, Z.; Stillman, M. J. Inorg. Chem. 1990, 29, 5101-5109
81. Gasyna, Z.; Browett, W. R.; Stillman, M. J. Inorg. Chem. 1988, 27, 4619-4622
82. Yu, R. P.; Darmon, J. M.; Milsmann, C.; Margulieux, G. W.; Stieber, S. C. E.; DeBeer, S.; Chirik, P. J. J. Am. Chem. Soc. 2013, 135, 13168-13184
83. Tomson, N. C.; Crimmin, M. R.; Petrenko, T.; Rosebrugh, L. E.; Sproules, S.; Boyd, W. C.; Bergman, R. G.; DeBeer, S.; Toste, F. D.; Wieghardt, K. J. Am. Chem. Soc. 2011, 133, 18785-18801