Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules

Journal of the American Chemical Society

Volumn 137, Issue 46, 2015, Pages 14590-14593

  Howell, Jennifer M ^a   Feng, Kaibo ^a   Clark, Joseph R ^a   Trzepkowski, Louis J ^a   White, M Christina ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; MOLECULES; NITROGEN;

FUNCTIONALIZATIONS; IRON CATALYST; LEWIS ACID; NATURAL PRODUCTS; NITROGEN HETEROCYCLES; NITROGEN-CONTAINING MOLECULES; PRIMARY AMINES; REMOTE OXIDATION;

OXIDATION;

AMINE; BRONSTED ACID; CARBON; HYDROGEN; IMIDE; LEWIS ACID; NITROGEN; PYRIDINE;

ARTICLE; CATALYST; CHEMICAL BOND; ENANTIOMER; OXIDATION; REACTION OPTIMIZATION; CHEMISTRY; OXIDATION REDUCTION REACTION;

CARBON; HYDROGEN; NITROGEN; OXIDATION-REDUCTION;

EID: 84948706674     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b10299     Document Type: Article

References (30)

1. Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257 10.1021/jm501100b
2. White, M. C. Science 2012, 335, 807 10.1126/science.1207661
3. Nam, W.; Lee, Y.-M.; Fukuzumi, S. Acc. Chem. Res. 2014, 47, 1146 10.1021/ar400258p
4. Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069 10.1039/b607547a
5. Catino, A. J.; Nichols, J. M.; Nettles, B. J.; Doyle, M. P. J. Am. Chem. Soc. 2006, 128, 5648 10.1021/ja061146m
6. Condie, A. G.; González-Gómez, J. C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2010, 132, 1464 10.1021/ja909145y
7. Hari, D. P.; König, B. Org. Lett. 2011, 13, 3852 10.1021/ol201376v
8. Noble, A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 11602 10.1021/ja506094d
9. He, J.; Hamann, L. G.; Davies, H. M. L.; Beckwith, R. E. J. Nat. Commun. 2015, 6, 5943 10.1038/ncomms6943
10. McNally, A.; Haffemayer, B.; Collins, B. S. L.; Gaunt, M. J. Nature 2014, 510, 129 10.1038/nature13389
11. Chan, K. S. L.; Wasa, M.; Chu, L.; Laforteza, B. N.; Miura, M.; Yu, J.-Q. Nat. Chem. 2014, 6, 146 10.1038/nchem.1836
12. Chen, M. S.; White, M. C. Science 2007, 318, 783 10.1126/science.1148597
13. Chen, M. S.; White, M. C. Science 2010, 327, 566 10.1126/science.1183602
14. Gormisky, P. E.; White, M. C. J. Am. Chem. Soc. 2013, 135, 14052 10.1021/ja407388y
15. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2006; pp 15-16.
16. Staubitz, A.; Robertson, A. P. M.; Sloan, M. E.; Manners, I. Chem. Rev. 2010, 110, 4023 10.1021/cr100105a
17. Malik, H. A.; Taylor, B. L. H.; Kerrigan, J. R.; Grob, J. E.; Houk, K. N.; Du Bois, J.; Hamann, L. G.; Patterson, A. W. Chem. Sci. 2014, 5, 2352 10.1039/c3sc53414f
18. Asensio, G.; González-Núñez, M. E.; Bernardini, C. B.; Mello, R.; Adam, W. J. Am. Chem. Soc. 1993, 115, 7250 10.1021/ja00069a025
19. Lee, M.; Sanford, M. S. J. Am. Chem. Soc. 2015, 137, 12796 10.1021/jacs.5b09099
20. Ferrer, M.; Sánchez-Baeza, F.; Messeguer, A.; Diez, A.; Rubiralta, M. J. Chem. Soc., Chem. Commun. 1995, 293 10.1039/c39950000293
21. Brennan, M. B.; Claridge, T. D. W.; Compton, R. G.; Davies, S. G.; Fletcher, A. M.; Henstridge, M. C.; Hewings, D. S.; Kurosawa, W.; Lee, J. A.; Roberts, P. M.; Schoonen, A. K.; Thomson, J. E. J. Org. Chem. 2012, 77, 7241 10.1021/jo3010556
22. Woodward, C. P.; Spiccia, N. D.; Jackson, W. R.; Robinson, A. J. Chem. Commun. 2011, 47, 779 10.1039/C0CC03716H
23. Hampe, E. M.; Rudkevich, D. M. Tetrahedron 2003, 59, 9619 10.1016/j.tet.2003.09.096
24. Zimmerman, D. M.; Nickander, R.; Horng, J. S.; Wong, D. T. Nature 1978, 275, 332 10.1038/275332a0
25. O'Hagan, D. Nat. Prod. Rep. 1997, 14, 637 10.1039/np9971400637
26. Gören, M. Z.; Onat, F. CNS Drug Rev. 2007, 13, 224 10.1111/j.1527-3458.2007.00009.x
27. Wu, Y.-H.; Rayburn, J. W.; Allen, L. E.; Ferguson, H. C.; Kissel, J. W. J. Med. Chem. 1972, 15, 477 10.1021/jm00275a009
28. Schmidt, V. A.; Quinn, R. K.; Brusoe, A. T.; Alexanian, E. J. J. Am. Chem. Soc. 2014, 136, 14389 10.1021/ja508469u
29. Luo, Y.-R.; Cheng, J.-P. In CRC Handbook of Chemistry & Physics, 94 th ed.; Haynes, W. M., Ed.; CRC Press: Boca Raton, FL, 2013; pp 9-65.
30. Kondo, H.; Oritani, T.; Yamashita, K. Agric. Biol. Chem. 1990, 54, 1531 10.1271/bbb1961.54.1531