Regioselective oxidation of nonactivated alkyl C-H groups using highly structured non-heme iron catalysts

Journal of Organic Chemistry

Volumn 78, Issue 4, 2013, Pages 1421-1433

  Gómez, Laura ^a   Canta, Merceì ^a   Font, David ^a   Prat, Irene ^a   Ribas, Xavi ^a   Costas, Miquel ^a  

^a UNIVERSITY OF GIRONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL DIAMINE; COMPLEX ORGANIC MOLECULES; COORDINATION COMPLEX; COORDINATION SITES; DONOR LIGANDS; IRON CATALYST; IRON CENTERS; ORGANIC MOLECULES; ORGANIC SYNTHESIS; OXIDATION PRODUCTS; OXIDATION REACTIONS; REGIOSELECTIVE OXIDATION; SELECTIVE OXIDATION; STERIC BULK; TERMINAL OXIDANTS; TETRADENTATE;

CATALYSTS; CATALYTIC OXIDATION; IRON; IRON COMPOUNDS; LIGANDS; MONOTERPENES; OXIDANTS; OXIDATION; PORPHYRINS; STEREOCHEMISTRY; X RAY DIFFRACTION ANALYSIS;

REGIOSELECTIVITY;

CARBENE; CARBON; COORDINATION COMPOUND; DIAMINE; HYDROGEN; IRON; PINENE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; DRUG ISOLATION; OXIDATION; X RAY DIFFRACTION;

EID: 84873960171     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302196q     Document Type: Article

References (76)

1. Chen, K.; Baran, P. S. Nature 2009, 459, 824
2. Maimone, T. J.; Baran, P. S. Nat. Chem. Biol 2007, 3, 396
3. Hanson, J. R. Nat. Prod. Rep. 2010, 27, 887
4. Zhang, K.; Shafer, B. M.; Matthew, D.; Demars, I.; Stern, H. A.; Fasan, R. J. Am. Chem. Soc. 2012, 134, 18695
5. Mendoza, A.; Ishihara, Y.; Baran, P. S. Nat. Chem. 2012, 4, 21
6. Wender, P. A.; Hilinski, M. K.; Mayweg, A. V. W. Org. Lett. 2005, 7, 79
7. Newhouse, T.; Baran, P. S. Angew. Chem., Int. Ed. 2011, 50, 3362
8. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976
9. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
10. Zhou, M.; Crabtree, R. H. Chem. Soc. Rev. 2011, 40, 1875
11. Lu, H.; Zhang, P. Chem. Soc. Rev. 2011, 40, 1899
12. Company, A.; Gomez, L.; Costas, M. In Iron-Containing Enzymes, Versatile Catalysts of Hydroxylation Reactions in Nature; De Visser, S. P.; Kumar, D., Eds.; Royal Society of Chemistry: Cambridge, U.K., 2011.
13. White, M. C. Science 2012, 335, 807
14. Shul'pin, G. B. Org. Biomol. Chem. 2010, 8, 4217
15. Lee, S.; Fuchs, P. L. J. Am. Chem. Soc. 2002, 124, 13978
16. Brodsky, B. H.; Du Bois, J. J. Am. Chem. Soc. 2005, 127, 15391
17. Curci, R.; D'Accolti, L.; Fusco, C. Acc. Chem. Res. 2006, 39, 1
18. Litvinas, N. D.; Brodsky, B. H.; Du Bois, J. Angew. Chem., Int. Ed. 2009, 4513
19. McNeill, E.; Bois, J. D. J. Am. Chem. Soc. 2010, 132, 10202
20. Tenaglia, A.; Terranova, E.; Waegell, B. J. Org. Chem. 1992, 57, 5523
21. McNeill, E.; Bois, J. D. Chem. Sci. 2012, 3, 1810
22. Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504
23. Barton, D. H. R.; Li, T.; Mackinnon, J. Chem. Commun. 1997, 557
24. Kamata, K.; Yonehara, K.; Nakagawa, Y.; Uehara, K.; Mizuno, N. Nat. Chem. 2010, 2, 478
25. Zhao, Y.; Yim, W.-L.; Tan, C. K.; Yeung, Y.-Y. Org. Lett. 2011, 13, 4308
26. Larsen, A. T.; May, E. M.; Auclair, K. J. Am. Chem. Soc. 2011, 133, 7853
27. Moreira, R. F.; Wehn, P. M.; Sames, D. Angew. Chem., Int. Ed. 2000, 39, 1618
28. Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542
29. Chen, K.; Richter, J. M.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 7247
30. Kasuya, S.; Kamijo, S.; Inoue, M. Org. Lett. 2009, 11, 3630
31. Simmons, E. M.; Hartwig, J. F. Nature 2011, 483, 70
32. Giri, R.; Liang, J.; Lei, J.-G.; Li, J.-J,; Wang, D.-H.; Chen, X.; Naggar, I. C.; Guo, C; Foxman, B. M.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 7420
33. Das, S.; Incarvito, C. D.; Crabtree, R. H.; Brudvig, G. W. Science 2006, 312, 1941
34. Bigi, M. A.; Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2012, 134, 9721
35. Zhang, S.-Y.; He, G.; Zhao, Y.; Wright, K.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2012, 134, 7313
36. Wang, Y.-F.; Chen, H.; Zhu, X.; Chiba, S. J. Am. Chem. Soc. 2012, 134, 11980
37. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293
38. Que, L.; Tolman, W. B. Nature 2008, 455, 333
39. Kovaleva, E. G.; Lipscomb, J. D. Nat. Chem. Biol. 2008, 4, 186
40. Bruijnincx, P. C. A.; Koten, G. v.; Gebbink, R. J. M. K. Chem. Soc. Rev. 2008, 12, 2716
41. Mukherjee, A.; Martinho, M.; Bominaar, E. L.; Munck, E.; Que, L. Angew. Chem., Int. Ed. 2009, 48, 1780
42. Comba, P.; Maurer, M.; Vadivelu, P. Inorg. Chem. 2009, 48, 10389
43. Yoon, J.; Wilson, S. A.; Jang, Y. K.; Seo, M. S.; Nehru, K.; Hedman, B.; Hodgson, K. O.; Bill, E.; Solomon, E. I.; Nam, W. Angew. Chem., Int. Ed. 2009, 48, 1257
44. Liu, P.; Liu, Y.; Wong, E. L.-M.; Xiang, S.; Che, C.-M. Chem. Sci. 2011, 2, 2187
45. Chen, K.; Que, L., Jr. J. Am. Chem. Soc. 2001, 123, 6327
46. Enthaler, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2008, 47, 3317
47. Correa, A.; Mancheno, O. G.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108
48. Costas, M.; Chen, K.; Que, L., Jr. Coord. Chem. Rev. 2000, 200-202, 517
49. Chen, M. S.; White, M. C. Science 2007, 318, 783
50. Company, A.; Gómez, L.; Fontrodona, X.; Ribas, X.; Costas, M. Chem. Eur. J. 2008, 14, 5727
51. Gomez, L.; Garcia-Bosch, I.; Company, A.; Benet-Buchholz, J.; Polo, A.; Sala, X.; Ribas, X.; Costas, M. Angew. Chem., Int. Ed. 2009, 48, 5720
52. Chen, M. S.; White, M. C. Science 2010, 327, 566
53. He, Y.; Gorden, J. D.; Goldsmith, C. R. Inorg. Chem. 2011, 50, 12651
54. Hitomi, Y.; Arakawa, K.; Funabiki, T.; Kodera, M. Angew. Chem., Int. Ed. 2012, 51, 3448
55. For a recent related manganese-based system see Ottenbacher, R. V.; Samsonenko, D. G.; Talsi, E. P.; Bryliakov, K. P. Org. Lett. 2012, 14, 4310
56. Knof, U.; von Zelewsky, A. Angew. Chem., Int. Ed. 1999, 38, 302
57. Costas, M.; Tipton, A. K.; Chen, K.; Jo, D.-H.; Que, L., Jr. J. Am. Chem. Soc. 2001, 123, 6722
58. Suzuki, K.; Oldenburg, P. D.; Que, L., Jr. Angew. Chem., Int. Ed. 2008, 47, 1887
59. Costas, M.; Que, L., Jr. Angew. Chem., Int. Ed. 2002, 12, 2179
60. Barton, D. H. R.; Bévière, S. D.; Chavasiri, W.; Csuhai, E.; Doller, D.; Liu, W.-G. J. Am. Chem. Soc. 1992, 114, 2147
61. Shul'pin, G. B.; Kozlov, Y. N.; Shul'pina, L. S.; Kudinov, A. R.; Mandelli, D. Inorg. Chem. 2009, 48, 10480
62. Shul'pin, G. B.; Kozlov, Y. N.; Shul'pina, L. S.; Petrovskiy, P. V. Appl. Organomet. Chem. 2010, 24, 464
63. Shul'pin, G. B.; Suss-Fink, G.; Smith, J. R. L. Tetrahedron 1999, 55, 5345
64. Chen, K.; Eschenmoser, A.; Baran, P. S. Angew. Chem., Int. Ed. 2009, 48, 9705
65. Cook, B. R.; Reinert, T. J.; Suslick, K. S. J. Am. Chem. Soc. 1986, 108, 7281
66. Battioni, P.; Renaud, J. P.; Bartoli, J. F.; Reina-Artiles, M.; Fort, M.; Mansuy, D. J. Am. Chem. Soc. 1988, 110, 8462
67. Barton, D. H. R.; Beloeil, J.-C.; Billion, A.; Boivin, J.; Lallemand, J.-Y.; Lelandais, P.; Mergui, S. Helv. Chim. Acta 1987, 70, 2187
68. Härtner, J.; Reinscheid, U. M. J. Mol. Struct. 2008, 872
69. Chapman, N. B.; Parker, R. E.; Smith, P. J. A. J. Chem. Soc. 1960, 3634
70. Cano, A.; Ramírez-Apan, M. T.; Delgado, G. J. Braz. Chem. Soc. 2011, 22, 1177
71. Liu, W.; Groves, J. T. J. Am. Chem. Soc. 2010, 132, 12847
72. Bartoli, J. F.; Brigaud, O.; Battioni, P.; Mansuy, D. J. Chem. Soc., Chem. Commun. 1991, 440
73. Wang, C.; Shalyaev, K. V.; Bonchio, M.; Carofiglio, T.; Groves, J. T. Inorg. Chem. 2006, 45, 4769
74. Groves, J. T.; Viski, P. J. Am. Chem. Soc. 1989, 111, 8537
75. Shiao, M.-J.; Lin, J. L.; Kuo, Y.-H.; Shih, K.-S. Tetrahedron Lett. 1986, 27, 4059
76. Choudhary, M. I.; Musharraf, S. G.; Sami, A.; Atta-ur-Rahman Helv. Chim. Acta 2004, 87, 2685