The Fe(PDP)-catalyzed aliphatic C-H oxidation: a slow addition protocol

Tetrahedron

Volumn 65, Issue 16, 2009, Pages 3078-3084

  Vermeulen, Nicolaas A ^a   Chen, Mark S ^a   Christina White, M ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; IRON DERIVATIVE; LIGAND; NATURAL PRODUCT;

ADDITION REACTION; ARTICLE; CATALYSIS; HYDROXYLATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 62049084096     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.11.082     Document Type: Article

References (55)

1. For some recent reviews on C-H bond functionalizations:
2. Muller P., and Fruit C. Chem. Rev. 103 (2003) 2905
3. Dick A.R., and Sanford M.S. Tetrahedron 62 (2006) 2439
4. Davies H.M.L., and Manning J.R. Nature 451 (2008) 417
5. Lewis J.C., Bergman R.G., and Ellman J.A. Acc. Chem. Res. 41 (2008) 1013
6. Alberico D., Scott M.E., and Lautens M. Chem. Rev. 107 (2007) 174
7. Allylic C-H to C-O:
8. Chen M.S., and White M.C. J. Am. Chem. Soc. 126 (2004) 1346
9. Chen M.S., Prabagaran N., Labenz N.A., and White M.C. J. Am. Chem. Soc. 127 (2005) 6970
10. Fraunhoffer K.J., Prabagaran N., Sirois L.E., and White M.C. J. Am. Chem. Soc. 128 (2006) 9032
11. Delcamp J.D., and White M.C. J. Am. Chem. Soc. 128 (2006) 15076
12. Allylic C-H to C-N:
13. Fraunhoffer K.J., and White M.C. J. Am. Chem. Soc. 129 (2007) 7274
14. Reed S.A., and White M.C. J. Am. Chem. Soc. 130 (2008) 3316
15. Allylic C-H to C-C:
16. Young A.J., and White M.C. J. Am. Chem. Soc. 130 (2008) 14090
17. Fraunhoffer K.J., Bachovchin D.A., and White M.C. Org. Lett. 7 (2005) 223
18. Covell D.J., Vermeulen N.A., Labenz N.A., and White M.C. Angew. Chem., Int. Ed. 45 (2006) 8217
19. For an excellent review see:
20. Hoffman R.W. Synthesis 21 (2006) 3531
21. 2 allylic oxidations in natural products synthesis, see:
22. Nicolaou K.C., Yang Z., Liu J.J., Ueno H., Nantermet P.G., Guy R.K., Claiborne C.F., Renaud J., Couladouros E.A., Paulvannan K., and Sorenson E.J. Nature 367 (1994) 630
23. Wender P.A., Jesudason C.D., Nakahira H., Tamura N., Tebbe A.L., and Ueno Y. J. Am. Chem. Soc. 119 (1997) 12976
24. For some recent examples, see:
25. Lee S., and Fuchs P.L. J. Am. Chem. Soc. 124 (2002) 13978
26. Wender P.A., Hilinski M.K., and Mayweg A.V.W. Org. Lett. 7 (2005) 79
27. Davies H.M.L., Dai X., and Long M.S. J. Am. Chem. Soc. 128 (2006) 2485
28. For some selected examples, see:
29. Wang D.-H., Wasa M., Giri R., and Yu J.-Q. J. Am. Chem. Soc. 130 (2008) 7190
30. Lafrance M., Blaquiere N., and Fagnou K. Eur. J. Org. Chem. (2007) 811
31. Das S., Incarvito C.D., Crabtree R.H., and Brudvig G.W. Science 312 (2006) 1941
32. O'Malley S.J., Tan K.L., Watzke A., Bergman R.G., and Ellman J.A. J. Am. Chem. Soc. 127 (2005) 13496
33. Hinman A., and Du Bois J. J. Am. Chem. Soc. 125 (2003) 11510
34. Breslow R., Baldwin S., Flechtner T., Kalicky P., Liu S., and Washburn W. J. Am. Chem. Soc. 95 (1973) 3251
35. Shevi R.A., Guerrero C.A., Shi J., Li C.-C., and Baran P.S. J. Am. Chem. Soc. 130 (2008) 7241
36. PDP indicates 2-({(S)-2-[(S)-1-(pyridin-2-ylmethyl)pyrrolidin-2-yl]pyrrolidin-1-yl}methyl)pyridine].
37. Chen M.S., and White M.C. Science 318 (2007) 783
38. For the first report of a related non-heme iron(mep) complex [mep=N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-ethane, 1,2-diamine] and its oxidation reactivity see:
39. Okuno T., Ito S., Ohba S., and Nishida Y. J. Chem. Soc., Dalton Trans. (1997) 3547
40. For mechanistic studies on Fe(mep) oxidations see:
41. Chen K., and Que Jr. L. Chem. Commun. (1999) 1375
42. For the first demonstration of a preparatively useful non-heme iron system see the Fe(mep) catalyzed epoxidation:
43. White M.C., Doyle A.G., and Jacobsen E.N. J. Am. Chem. Soc. 123 (2001) 7194
44. For some examples of non-directed aliphatic C-H oxidation reactions with simple hydrocarbon substrates see:
45. Murray R.W., Jeyaraman R., and Mohan L. J. Am. Chem. Soc. 108 (1986) 2470
46. Mello R., Fiorentino M., Fusco C., and Curci R. J. Am. Chem. Soc. 111 (1989) 6749
47. DesMarteau D.D., Donadelli A., Montanari V., Petrov V.A., and Resnati G. J. Am. Chem. Soc. 115 (1993) 4897
48. Labinger J.A., and Bercaw J.E. Nature 417 (2002) 507 and references therein
49. Brodsky B.H., and Du Bois J. J. Am. Chem. Soc. 127 (2005) 15391
50. Ref. 5a.;
51. Ref. 9a.
52. For the first demonstration of the importance of carboxylic acid additives in non-heme iron catalyzed oxidations, see Ref. 9c.
53. We have not observed decreases in catalyst 1 hydroxylation activity after ca. 1 year storage at 0 °C.
54. Jensen M.P., Mehn M.P., and Que Jr. L. Angew. Chem., Int. Ed. 42 (2003) 4357
55. For full characterization see:. Martin D.D., Marcos I.S., Basabe P., Romero R.E., Moro R.F., Lumeras W., Rodriguez L., and Urones J.G. Synthesis 7 (2001) 1013