Regiospecific ortho-aromatic hydroxylation via cyclonickelation using hydrogen peroxide and other oxygen donors: Synthesis of metalloazosalophens

European Journal of Inorganic Chemistry

Volumn , Issue 27, 2007, Pages 4263-4271

  Pattanayak, Poulami ^a   Pratihar, Jahar Lal ^a   Patra, Debprasad ^a   Burrows, Andrew ^b   Mohan, Mary ^b   Chattopadhyay, Surajit ^a  

^a UNIVERSITY OF KALYANI   (India)

^b UNIVERSITY OF BATH   (United Kingdom)

Author keywords

C H activation; Metallacycles; N,O ligands; Nickel; Oxygenation; Peroxo reagents

Indexed keywords

ACTIVATION ANALYSIS; CHELATION; CHLORINE COMPOUNDS; GEOMETRY; HYDROGEN PEROXIDE; HYDROXYLATION; NICKEL COMPOUNDS; OXIDATION; OXYGEN;

2- ANILINES; AROMATIC HYDROXYLATION; ARYL GROUP; C-H ACTIVATION; METALLACYCLES; N,O LIGAND; O LIGANDS; OXYGEN DONORS; PEROXO REAGENT; REGIOSPECIFIC;

LIGANDS;

EID: 34948819621     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200700149     Document Type: Article

References (60)

1. a) H. Zhou, S. T. Nguyen, Inorg. Chem. 2004, 43, 4315;
2. b) E. F. DiMauro, A. Mamai, M. C. Kozlowski, Organometallics 2003, 22, 850;
3. c) K. J. Miller, J. H. Baag, M. M. Abu-Omar, Inorg. Chem. 1999, 38, 4510.
4. a) E. M. McGarrile, D. G. Gilheany, Chem. Rev. 2005, 105, 1563;
5. b) K. P. Bryliakov, E. P. Talsi, Inorg. Chem. 2003, 42, 7258.
6. a) M. Costas, M. P. Mehn, M. P. Jensen Jr, L. Que, Chem. Rev. 2004, 104, 939;
7. b) X. Zhou, J. Shearer, S. E. Rotika, J. Am. Chem. Soc. 2000, 122, 9046;
8. c) J. E. Reed, A. A. Arnal, S. Neidle, R. Vilar, J. Am. Chem. Soc. 2006, 128, 5992.
9. a) S. Karmakar, S. B. Choudhury, S. Ganguly, A. Chakravorty, J. Chem. Soc. Dalton Trans. 1997, 585 and references cited therein;
10. b) A. H. Velders, H. Kooijman, A. L. Spek, J. G. Haasnoot, D. de Vos, J. Reedijk, Inorg. Chem. 2000, 39, 2966;
11. c) A. C. G. Hotze, E. P. L. van der Geer, S. E. Caspers, H. Kooijman, A. L. Spek, J. G. Haasnoot, J. Reedijk, Inorg. Chem. 2004, 43, 4935;
12. d) T. Yitaka, M. Kurihara, K. Kubo, H. Nishihara, Inorg. Chem. 2000, 39, 3438;
13. e) K. K. Kamar, S. Das, C.-H. Hung, A. Castineiras, M. D. Kuzmin, C. Rillo, J. Bartolome, S. Goswami, Inorg. Chem. 2003, 42, 5367;
14. f) C. Das, S.-M. Peng, G.-H. Lee, S. Goswami, New J. Chem. 2002, 26, 222;
15. g) T. K. Misra, T. K. Das, C. Sinha, P. Ghosh, C. K. Pal, Inorg. Chem. 1998, 37, 1672.
16. J. L. Zhu, N. P. Grigoriadis, J. P. Lee, J. A. Porco, J. Am. Chem. Soc. 2005, 127, 9342.
17. a) R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, ch. 4.1;
18. b) E. N. Jacobsen in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, ch. 4.2;
19. c) T. Katsuki, Adv. Synth. Catal. 2002, 344, 131;
20. d) T. Katsuki, Coord. Chem. Rev. 1995, 140, 189;
21. e) T. Katsuki, J. Mol. Catal. A 1996, 113, 87;
22. f) C. T. Dalton, K. M. Ryan, V. M. Wall, C. Bousquet, D. G. Gilheany, Top. Catal. 1998, 5, 75;
23. g) D. R. Kelly, S. M. Roberts, Biopolymers 2006, 84, 74;
24. h) L. Canalai, D. C. Sherrington, Chem. Soc. Rev. 1999, 28, 85.
25. a) M. Lersch, M. Tilset, Chem. Rev. 2005, 105, 2471 and references cited therein;
26. b) J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527 and references cited therein;
27. c) P. Bandyopadhyay, D. Bandyopadhyay, A. Chakravorty, F. A. Cotton, L. R. Fakvello, S. Han, J. Am. Chem. Soc. 1983, 105, 6327;
28. d) S. Chattopadhyay, C. Sinha, P. Basu, A. Chakravorty, Organometallics 1991, 10, 1135;
29. e) S. Chattopadhyay, C. Sinha, P. Basu, A. Chakravorty, J. Organomet. Chem. 1991, 414, 421;
30. f) J. Pratihar, N. Maiti, P. Pattanayak, S. Chattopadhyay, Polyhedron 2005, 24, 1953.
31. a) I. Omae, Chem. Rev. 1979, 79, 287;
32. b) J. P. Kleiman, M. Dubeck, J. Am. Chem. Soc. 1963, 85, 1544;
33. c) M. Ghedini, D. Pucci, A. Crispini, G. Barberio, Organometallics 1999, 18, 2116;
34. d) T. Kawamoto, Y. Kushi, Bull. Chem. Soc. Jpn. 2004, 77, 289;
35. e) G. K. Anderson, R. J. Cross, K. W. Muir, L. M. Muir, J. Organomet. Chem. 1989, 362, 225.
36. A. C. Cope, R. W. Siekman, J. Am. Chem. Soc. 1965, 87, 3272.
37. a) K. Koo, G. L. Hillhouse, Organometallics 1998, 17, 2924;
38. b) P. T. Matsunaga, G. L. Hillhouse, J. Am. Chem. Soc. 1993, 115, 2075;
39. c) P. T. Matsunaga, J. C. Mavropoulos, G. L. Hillhouse, Polyhedron 1995, 14, 175;
40. d) M. A. Bennett, M. Glewis, D. C. R. Hockless, E. Wenger, J. Chem. Soc. Dalton Trans. 1997, 3105.
41. J. Cámpora, P. Palma, E. Carmona, Coord. Chem. Rev. 1999, 193-195, 207.
42. I. W. C. E. Arends, Angew. Chem. Int. Ed. 2006, 45, 6250.
43. I. W. C. E. Arends, R. A. Sheldon, Top. Catal. 2002, 19, 133.
44. a) F. Zaera, J. M. Guevermont, N. R. Gleason, J. Phys. Chem. B 2001, 105, 2257;
45. b) N. Gleason, J. Goevermont, F. Zaera, J. Phys. Chem. B 2003, 107, 11133 and references cited therein.
46. [7c,7d]
47. sa l)Ni is available as Supporting Information (Figure S24).
48. P. L. Alsters, H. T. Teunissen, J. Boersma, A. L. Spek, G. van Koten, Organometallics 1993, 12, 4691.
49. a) J. F. Kinneary, J. S. Albert, C. J. Burrows, J. Am. Chem. Soc. 1988, 110, 6124;
50. b) J. D. Koola, J. K. Kochi, Inorg. Chem. 1987, 26, 908.
51. R. H. Holm, Chem. Rev. 1987, 87, 1401.
52. M. Kujime, S. Hikichi, M. Akita, Dalton Trans. 2003, 3506.
53. M. Fieser, L. F. Fieser, Reagents for Organic Synthesis, Wiley-Interscience,New York, 1971, vol. 3.
54. a) T. Giaser, M. Heidemeier, T. Lügger, Dalton Trans. 2003, 2381;
55. b) B. Bosnich, J. Am. Chem. Soc. 1968, 90, 627.
56. N. Maiti, S. Pal, S. Chattopadhyay, Inorg. Chem. 2001, 40, 2204.
57. J. Wang, F. L. Bei, X. Y. Xu, X. J. Yang, X. Wang, J. Chem. Crystallogr. 2003, 33, 845.
58. E. Dunach, A. P. Esteves, L. F. M. Leite, M. A. Lemos, M. J. Medeiros, S. Olivero, Port. Electrochim. Acta 2003, 21, 191.
59. a) P. Chattopadhyay, M. K. Nayak, S. P. Bhattacharya, C. Sinha, Polyhedron 1997, 16, 1291;
60. b) F. Basuli, P. Chattopadhyay, C. Sinha, Polyhedron 1996, 15, 2439.