Iron(II)-catalyzed intermolecular amino-oxygenation of olefins through the N - O bond cleavage of functionalized hydroxylamines

Journal of the American Chemical Society

Volumn 136, Issue 38, 2014, Pages 13186-13189

  Lu, Deng Fu ^a   Zhu, Cheng Liang ^a   Jia, Zhen Xin ^a   Xu, Hao ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; CHEMICAL REACTIONS; IRON; IRON COMPOUNDS; OLEFINS; OXYGENATION; REACTION KINETICS;

ALCOHOL DERIVATIVES; BOND CLEAVAGES; DIASTEREOSELECTIVE; FUNCTIONALIZED; HYDROXYLAMINE DERIVATIVE;

AMINATION;

ALKENE DERIVATIVE; AMINOALCOHOL; FERROUS ION; HYDROXYLAMINE; OXIDIZING AGENT; ALKENE; IRON;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CONTROLLED STUDY; OXYGENATION; STEREOCHEMISTRY; CHEMISTRY; STEREOISOMERISM;

ALKENES; AMINATION; CATALYSIS; HYDROXYLAMINES; IRON; OXIDANTS; STEREOISOMERISM;

EID: 84912563134     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja508057u     Document Type: Article

References (62)

1. (a) Sharpless, K. B.; Chong, A. O.; Oshima, K. J. Org. Chem. 1976, 41, 177.
2. (b) Li, G. G.; Chang, H. T.; Sharpless, K. B. Angew. Chem., Int. Ed. 1996, 35, 451.
3. (a) Fuller, P. H.; Kim, J.-W.; Chemler, S. R. J. Am. Chem. Soc. 2008, 130, 17638.
4. (b) Paderes, M. C.; Chemler, S. R. Org. Lett. 2009, 11, 1915.
5. (c) Sequeira, F. C.; Chemler, S. R. Org. Lett. 2012, 14, 4482.
6. (d) Turnpenny, B. W.; Chemler, S. R. Chem. Sci. 2014, 5, 1786.
7. (e) Michaelis, D. J.; Shaffer, C. J.; Yoon, T. P. J. Am. Chem. Soc. 2007, 129, 1866.
8. (f) Benkovics, T.; Guzei, I. A.; Yoon, T. P. Angew. Chem., Int. Ed. 2010, 49, 9153.
9. (g) Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2010, 132, 4570.
10. (h) Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2012, 134, 12370.
11. (i) Alexanian, E. J.; Lee, C.; Sorensen, E. J. J. Am. Chem. Soc. 2005, 127, 7690.
12. (j) Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 7179.
13. (k) Desai, L. V.; Sanford, M. S. Angew. Chem., Int. Ed. 2007, 46, 5737.
14. (l) Weinstein, A. B.; Schuman, D. P.; Tan, Z. X.; Stahl, S. S. Angew. Chem., Int. Ed. 2013, 52, 11867.
15. (m) Zhu, H.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2014, 136, 1766.
16. (n) Muñiz, K.; Iglesias, A.; Fang, Y. Chem. Commun. 2009, 5591.
17. (o) de Haro, T.; Nevado, C. Angew. Chem., Int. Ed. 2011, 50, 906.
18. (p) Wardrop, D. J.; Bowen, E. G.; Forslund, R. E.; Sussman, A. D.; Weerasekera, S. L. J. Am. Chem. Soc. 2010, 132, 1188.
19. (q) Lovick, H. M.; Michael, F. E. J. Am. Chem. Soc. 2010, 132, 1249.
20. (r) Schmidt, V. A.; Alexanian, E. J. J. Am. Chem. Soc. 2011, 133, 11402.
21. (s) Xu, H.-C.; Moeller, K. D. J. Am. Chem. Soc. 2008, 130, 13542.
22. (t) Donohoe, T. J.; Johnson, P. D.; Cowley, A.; Keenan, M. J. Am. Chem. Soc. 2002, 124, 12934.
23. (u) Harris, L.; Mee, S. P. H.; Furneaux, R. H.; Gainsford, G. J.; Luxenburger, A. J. Org. Chem. 2011, 76, 358.
24. (v) Farid, U.; Wirth, T. Angew. Chem., Int. Ed. 2012, 51, 3462.
25. (w) Mahoney, J. M.; Smith, C. R.; Johnston, J. N. J. Am. Chem. Soc. 2005, 127, 1354.
26. (x) Zhang, B.; Studer, A. Org. Lett. 2013, 15, 4548.
27. (a) Levites-Agababa, E.; Menhaji, E.; Perlson, L. N.; Rojas, C. M. Org. Lett. 2002, 4, 863.
28. (b) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137.
29. (c) Mulcahy, J. V.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 12630.
30. (d) Beaumont, S.; Pons, V.; Retailleau, P.; Dodd, R. H.; Dauban, P. Angew. Chem., Int. Ed. 2010, 49, 1634.
31. (e) Gigant, N.; Dequirez, G.; Retailleau, P.; Gillaizeau, I.; Dauban, P. Chem. - Eur. J. 2012, 18, 90.
32. (f) Dequirez, G.; Ciesielski, J.; Retailleau, P.; Dauban, P. Chem. - Eur. J. 2014, 20, 8929. For a manganese-mediated stoichiometric method, see:
33. (g) Du Bois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M. J. Am. Chem. Soc. 1997, 119, 3179.
34. (a) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598.
35. (b) Zalatan, D. N.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 9220.
36. (c) Nguyen, Q.; Sun, K.; Driver, T. G. J. Am. Chem. Soc. 2012, 134, 7262. For selected references of olefin aziridination through Cu and Rh metallonitrenes, see:
37. (d) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326.
38. (e) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
39. (f) Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672.
40. (g) Lebel, H.; Lectard, S.; Parmentier, M. Org. Lett. 2007, 9, 4797.
41. (h) Jat, J. L.; Paudyal, M. P.; Gao, H.; Xu, Q.-L.; Yousufuddin, M.; Devarajan, D.; Ess, D. H.; Kürti, L.; Falck, J. R. Science 2014, 343, 61.
42. (a) Breslow, R.; Gellman, S. H. J. Chem. Soc., Chem. Commun. 1982, 1400.
43. (b) Mahy, J. P.; Battioni, P.; Mansuy, D. J. Am. Chem. Soc. 1986, 108, 1079.
44. (c) Nakanishi, M.; Salit, A. F.; Bolm, C. Adv. Synth. Catal. 2008, 350, 1835.
45. (d) Paradine, S. M.; White, M. C. J. Am. Chem. Soc. 2012, 134, 2036.
46. (e) Hennessy, E. T.; Betley, T. A. Science 2013, 340, 591.
47. (f) Liu, Y.; Guan, X.; Wong, E. L.-M.; Liu, P.; Huang, J.-S.; Che, C.-M. J. Am. Chem. Soc. 2013, 135, 7194.
48. (g) Bach, T.; Schlummer, B.; Harms, K. Chem. Commun. 2000, 287.
49. (h) Churchill, D. G.; Rojas, C. M. Tetrahedron Lett. 2002, 43, 7225.
50. (a) Liu, G.-S.; Zhang, Y.-Q.; Yuan, Y.-A.; Xu, H. J. Am. Chem. Soc. 2013, 135, 3343.
51. (b) Zhang, Y.-Q.; Yuan, Y.-A.; Liu, G.-S.; Xu, H. Org. Lett. 2013, 15, 3910.
52. (c) Lu, D.-F.; Liu, G.-S.; Zhu, C.-L.; Yuan, B.; Xu, H. Org. Lett. 2014, 16, 2912.
53. For leading references of chiral BOX and relevant ligands, see: (a) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
54. (b) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
55. (c) Nishikawa, Y.; Yamamoto, H. J. Am. Chem. Soc. 2011, 133, 8432.
56. Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 5811.
57. Osmium-based aminohydroxylation of indene affords racemic mixtures of 1- and 2-amino indanols; see: (a) Masruri; Willis, A. C.; McLeod, M. D. J. Org. Chem. 2012, 77, 8480. For an indirect method of 2-amino indanol synthesis, see:
58. (b) Corey, E. J.; Roper, T. D.; Ishihara, K.; Sarakinos, G. Tetrahedron Lett. 1993, 34, 8399.
59. Davies, I. W.; Gerena, L.; Lu, N.; Larsen, R. D.; Reider, P. J. J. Org. Chem. 1996, 61, 9629.
60. Lee, N. H.; Jacobsen, E. N. Tetrahedron Lett. 1991, 32, 6533.
61. (a) Kharasch, M. S.; Sosnovsky, G. J. Am. Chem. Soc. 1958, 80, 756.
62. (b) Kochi, J. K. Science 1967, 155, 415.