Four-coordinate cobalt pincer complexes: Electronic structure studies and ligand modification by homolytic and heterolytic pathways

Journal of the American Chemical Society

Volumn 136, Issue 25, 2014, Pages 9211-9224

  Semproni, Scott P ^a   Milsmann, Carsten ^a   Chirik, Paul J ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; COBALT; COBALT COMPOUNDS; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRONIC STRUCTURE; HYDRIDES; LIGANDS; METAL IONS; SYNTHESIS (CHEMICAL);

ATOM ABSTRACTION; BOND-DISSOCIATION FREE ENERGIES; COBALT CHLORIDES; DFT COMPUTATIONS; EPR SPECTROSCOPY; HYDRIDE COMPLEXES; PINCER COMPLEXES; STABLE NITROXYL RADICALS;

CHLORINE COMPOUNDS;

2,2,6,6 TETRAMETHYLPIPERIDIN 1 YLOXIDANYL; ALKYNE; CARBON; CHELATE; CHLORIDE; COBALT COMPLEX; HYDROGEN; LIGAND; METAL ION; RADICAL; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CHEMICAL STRUCTURE; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; DISSOCIATION; ELECTRON SPIN RESONANCE; ENERGY; HYDROGEN BOND; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THERMOSTABILITY; X RAY DIFFRACTION;

EID: 84903292571     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja504334a     Document Type: Article

References (77)

1. The Chemistry of Pincer Compounds; Morales-Morales, D., Jensen, C. M., Eds.; Elsevier: Amsterdam, 2007.
2. Gunanathan, C.; Milstein, D. Acc. Chem. Res. 2011, 44, 588
3. Haneline, M. R.; Heyduk, A. F. J. Am. Chem. Soc. 2006, 128, 8410
4. Chirik, P. J.; Weighardt, K. Science 2010, 327, 794
5. Mazzacano, T. J.; Mankad, N. P. J. Am. Chem. Soc. 2013, 135, 17258
6. Grutzmacher, H.-J. Angew. Chem., Int. Ed. 2008, 47, 1814
7. Vogt, M.; Gargir, M.; Iron, M. A.; Diskin-Posner, Y.; Ben-David, Y.; Milstein, D. Chem.-Eur. J. 2012, 18, 9194
8. Bichler, B.; Holzhacker, C.; Stoger, B.; Puchberger, M.; Veiros, L. F.; Kirchner, K. Organometallics 2013, 32, 4414
9. Alberico, E.; Sponholz, P.; Cordes, C.; Nielsen, M.; Drexler, H.-J.; Baumann, W.; Junge, H.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 14162
10. Monfette, S.; Turner, Z. R.; Semproni, S. P.; Chirik, P. J. J. Am. Chem. Soc. 2012, 134, 4561
11. Prokopchuk, D. E.; Morris, R. H Organometallics 2012, 31, 7375
12. Mikhailine, A. A.; Maishan, M. I.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2012, 134, 12266
13. Bauer, G.; Kirchner, K. A. Angew. Chem., Int. Ed. 2011, 50, 5798
14. Langer, R.; Iron, M. A.; Lonstantinovski, L.; Diskin-Posner, Y.; Leitus, G.; Ben-David, Y.; Milstein, D. Chem.-Eur. J. 2012, 18, 7196
15. Casey, C. P.; Guan, H. J. Am. Chem. Soc. 2007, 129, 5816
16. Zou, W.; Lough, A. J.; Li, Y. F.; Morris, R. H. Science 2013, 342, 1080
17. Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord. Chem. Rev. 2004, 248, 2201
18. Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300
19. Tanaka, R.; Yamashita, M.; Nozaki, K. J. Am. Chem. Soc. 2009, 131, 14168
20. Langer, R.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50, 9948
21. Milstein, D. Top. Catal. 2010, 53, 915
22. Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 2005, 127, 10840
23. Gunanathan, C.; Ben-David, Y.; Milstein, D. Science 2007, 317, 790
24. Gnanaprakasam, B.; Zhang, J.; Milstein, D. Angew. Chem., Int. Ed. 2010, 48, 1468
25. Gnanaprakasam, B.; Milstein, D. J. Am. Chem. Soc. 2011, 133, 1682
26. Käss, M.; Friedrich, A.; Dress, M.; Schneider, S. Angew. Chem., Int. Ed. 2009, 48, 905
27. Knijnenburg, Q.; Gambarotta, S.; Budzelaar, P. H. M. Dalton Trans. 2006, 5442
28. Chirik, P. J. Inorg. Chem. 2011, 50, 9737
29. Tellman, K. P.; Humphries, M. J.; Rzepa, H. S.; Gibson, V. C. Organometallics 2004, 23, 5503
30. Knijnenburg, Q.; Hetterscheid, D.; Kooistra, T. M.; Budzelaar, P. H. M. Eur. J. Inorg. Chem. 2004, 1204
31. Bowman, A. C.; Milsmann, C.; Atienza, C. C. H.; Lobkovsky, E.; Wieghardt, K.; Chirik, P. J. J. Am. Chem. Soc. 2010, 132, 1676
32. Knijnenburg, Q.; Horton, A. D.; van der Heijden, H.; Kooistra, T. M.; Hetterscheid, D. G. H.; Smits, J. M. M.; de Bruin, B.; Budzelaar, P. H. M.; Gal, A. W. J. Mol. Catal. A: Chem. 2005, 232, 151
33. Obligacion, J. V.; Chirik, P. J. J. Am. Chem. Soc. 2013, 135, 19107
34. Yu, R. P.; Darmon, J. M.; Hoyt, J. M.; Margulieux, G. W.; Turner, Z. R.; Chirik, P. J. ACS Catal. 2012, 2, 1760
35. Atienza, C. C. H.; Tondreau, A. M.; Weller, K. J.; Lewis, K. M.; Cruse, R. W.; Nye, S. A.; Boyer, J. L.; Delis, J. G. P.; Chirik, P. J. ACS Catal. 2012, 2, 2169
36. Danopoulos, A. A.; Wright, J. A.; Motherwell, W. B.; Ellwood, S. Organometallics 2004, 23, 4807
37. 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
38. Zhang, G.; Scott, B. L.; Hanson, S. K. Angew. Chem., Int. Ed. 2012, 51, 12102
39. Zhang, G.; Hanson, S. K. Org. Lett. 2013, 15, 650
40. Zhang, G.; Vasudevan, K. V.; Scott, B. L.; Hanson, S. K. J. Am. Chem. Soc. 2013, 135, 8668
41. Moulton, C. J.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1976, 1020
42. Gupta, M.; Hagen, C.; Flesher, R. J.; Kaska, W. C.; Jensen, C. M. Chem. Commun. 1996, 2083
43. van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759
44. van der Vlugt, J. L.; Reek, J. N. H. Angew. Chem., Int. Ed. 2009, 48, 8832
45. Gunanathan, C.; Gnanaprakasam, B.; Iron, M. A.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2010, 132, 14763
46. Kloek, S. M.; Heinekey, D. M.; Goldberg, K. I. Angew. Chem., Int. Ed. 2007, 46, 4736
47. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255
48. Trovitch, R. J.; Lobkovsky, E.; Chirik, P. J. Inorg. Chem. 2006, 45, 7252
49. Pelczar, E. M.; Emge, T. J.; Krogh-Jespersen, K.; Goldman, A. S. Organometallics 2008, 27, 5759
50. Danopoulos, A. A.; Wright, J. A.; Motherwell, W. B. Chem. Commun. 2005, 784
51. For related iron carbonyl compounds with bis(phosphine) pyridine pincers with amino rather than methylene linkers see: Bichler, B.; Holzhacker, C.; Stöger; Puchberger, M.; Veiros, L. F.; Kirchner, K. Organometallics 2013, 32, 4114
52. Semproni, S. P.; Atienza, C. C. H.; Chirik, P. J. Chem. Sci. 2014, 5, 1956
53. 2 oxidative addition chemistry with cobalt pincers see: Rozenel, S. S.; Padilla, R.; Camp, C.; Arnold, J. Chem. Commun. 2014, 50, 2612
54. Obligacion, J. V.; Semproni, S. P.; Chirik, P. J. J. Am. Chem. Soc. 2014, 136, 4133
55. Khaskin, E.; Diskin-Posner, Y.; Weiner, L.; Leitus, G.; Milstein, D. Chem. Commun. 2013, 2771
56. Kaesz, H. D.; Saillant, R. B. Chem. Rev. 1972, 72, 233
57. Feller, M.; Ben-Ari, E.; Gupta, T.; Shimon, L. J. W.; Leitus, G.; Diskin-Posner, E.; Weiner, L.; Milstein, D. Inorg. Chem. 2007, 46, 10479
58. Atienza, C. C. H.; Milsmann, C.; Semproni, S. P.; Turner, Z. R.; Chirik, P. J. Inorg. Chem. 2013, 52, 5403
59. Ben-Ari, E.; Leitus, G.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2006, 128, 15390
60. Warren, J. J.; Tronic, T. A.; Mayer, J. M. Chem. Rev. 2010, 110, 6961
61. Maki, A. H.; Edelstein, N.; Davison, A.; Holm, R. H. J. Am. Chem. Soc. 1964, 86, 4580
62. Nishida, Y.; Sumita, A.; Kida, S. Bull. Chem. Soc. Jpn. 1977, 50, 759143
63. Nishida, Y.; Kida, S. Bull. Chem. Soc. Jpn. 1978, 51, 143
64. Nishida, Y.; Hayashi, K.; Sumita, A.; Kida, S. Bull. Chem. Soc. Jpn. 1980, 53, 271
65. Przyojski, J. A.; Arman, H. D.; Tonzetich, Z. J. Organometallics 2013, 32, 723
66. Lazzaro, D. P.; Fanwick, P. E.; McMillin, D. R. Inorg. Chem. 2012, 51, 10474
67. Vuzman, D.; Poverenov, E.; Shimon, L. J. W.; Diskin-Posner, Y.; Milstein, D. Organometallics 2008, 27, 2627
68. van der Vlugt, J. I.; Siegler, M. A.; Janssen, M.; Vogt, D.; Spek, A. L. Organometallics 2009, 28, 7025
69. Feller, M.; Ben-Ari, E.; Iron, M. A.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Konstantinovski, L.; Milstein, D. Inorg. Chem. 2010, 49, 1615
70. Vogt, M.; Rivada-Wheelaghan, O.; Iron, M. A.; Leitus, G.; Diskin-Posner, Y.; Shimon, L. J. W.; Ben-David, Y.; Milstein, D. Organometallics 2013, 32, 300
71. van der Vlugt, J. I.; Lutz, M.; Pidko, E. A.; Vogt, D.; Spek, A. L. Dalton Trans. 2009, 1016
72. van der Vlugt, J. I.; Pidko, E. A.; Bauer, R. C.; Gloaguen, Y.; Rong, M. K.; Lutz, M. Chem.-Eur. J. 2011, 17, 3850
73. Neese, F. Orca-an ab initio, DFT and Semiempirical Electronic Structure Package, Version 2.8, Revision 2287; Institut für Physikalische und Theoretische Chemie, Universität Bonn: Bonn (Germany), 2010.
74. Gloaguen, Y.; Rebreyend, C.; Lutz, M.; Kumar, P.; Huber, M.; Schneider, S.; de Bruin, B. Angew. Chem., Int. Ed. 2014, 10.1002/anie.201403445
75. Milsmann, C.; Patra, G. K.; Bill, E.; Weyhermüller, T.; DeBeer George, S.; Wieghardt, K. Inorg. Chem. 2009, 48, 7430
76. Milsmann, C.; Bill, E.; Weyhermüller, T.; DeBeer George, S.; Wieghardt, K. Inorg. Chem. 2009, 48, 9754
77. Warren, J. J.; Tronic, T. A.; Mayer, J. M. Chem. Rev. 2010, 110, 6961