Organocatalytic C-H hydroxylation with Oxone® enabled by an aqueous fluoroalcohol solvent system

Chemical Science

Volumn 5, Issue 2, 2014, Pages 656-659

  Adams, Ashley M ^a   Du Bois, J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C-H BOND OXIDATIONS; CATALYST SYSTEM; HYDROCARBON SUBSTRATES; HYDROXYLATION REACTIONS; ORGANOCATALYTIC; SOLVENT MIXTURES; SOLVENT SYSTEM; TERMINAL OXIDANTS;

CATALYSTS; SOLVENTS;

HYDROXYLATION;

EID: 84891445593     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc52649f     Document Type: Article

References (46)

1. T. Newhouse and P. B. Baran, Angew. Chem., Int. Ed., 2011, 50, 3362.
2. M. C. White, Science, 2012, 335, 807.
3. M. Costas, K. Chen and L. Que, Coord. Chem. Rev., 2000, 200, 517.
4. E. McNeill and J. Du Bois, Chem. Sci., 2012, 3, 1810.
5. E. McNeill and J. Du Bois, J. Am. Chem. Soc., 2010, 132, 10202.
6. M. S. Chen and M. C. White, Science, 2007, 318, 783.
7. M. S. Chen and M. C. White, Science, 2010, 327, 566.
8. M. A. Bigi, S. A. Reed and M. C. White, J. Am. Chem. Soc., 2012, 134, 9721.
9. D. Wang, et al., Chem. Sci., 2013, 4, 282.
10. Y. Hitomi, K. Arakawa, T. Funabiki and M. Kodera, Angew. Chem., Int. Ed. Engl., 2012, 51, 3448.
11. I. Prat, et al., Nat. Chem., 2011, 3, 788.
12. L. Gómez, et al., Angew. Chem., Int. Ed. Engl., 2009, 48, 5720.
13. S. Lee and P. L. Fuchs, J. Am. Chem. Soc., 2012, 124, 13978.
14. N. C. Deno, et al., Tetrahedron, 1977, 33, 2503.
15. C. Yuan, et al., Nature, 2013, 499, 192.
16. R. Curci and L. D'Accolti, Acc. Chem. Res., 2006, 39, 1.
17. L. Zou, et al., J. Org. Chem., 2013, 78, 4037.
18. K. Chen and P. S. Baran, Nature, 2009, 459, 824.
19. C. Annese, et al., J. Org. Chem., 2010, 75, 4812.
20. P. A. Wender, M. K. Hilinski and A. V. W. Mayweg, Org. Lett., 2002, 7, 79.
21. D. D. DesMarteau, A. Donadelli, V. Montanari, V. A. Petrov and G. Resnati, J. Am. Chem. Soc., 1993, 115, 4897.
22. D. D. DesMarteau, V. A. Petrov, V. Montanari, M. Pregnolato and G. Resnati, J. Fluorine Chem., 1992, 58, 339.
23. H. Mikula, et al., Org. Process Res. Dev., 2013, 17, 313.
24. J. O. Edwards, R. H. Pater, R. Curci and F. D. Furia, Photochem. Photobiol., 1979, 30, 63.
25. S. E. Denmark, D. C. Forbes, D. S. Hays, J. S. DePue and R. G. Wilde, J. Org. Chem., 1995, 60, 1391.
26. D. Yang, Acc. Chem. Res., 2004, 37, 497.
27. S. E. Denmark, Z. Wu and C. M. Crudden, J. Org. Chem., 1997, 62, 8288.
28. S. E. Denmark and H. Matsuhashi, J. Org. Chem., 2002, 67, 3479.
29. B. H. Brodsky and J. Du Bois, J. Am. Chem. Soc., 2005, 127, 15391.
30. N. D. Litvinas, B. H. Brodsky and J. Du Bois, Angew. Chem., Int. Ed. Engl., 2009, 48, 4513.
31. The half-life for dimethyldioxirane in aqueous solutions is less than that in organic solvent, see: J. Bouchard, C. Maine, R. M. Berry and D. S. Argyropoulos, Can. J. Chem., 1996, 74, 232.
32. D. Hong, M. Hoshino, R. Kuboi and Y. Goto, J. Am. Chem. Soc., 1999, 121, 8427.
33. B. Czarnik-Matusewicz, S. Pilorz, L.-P. Zhang and Y. Wu, J. Mol. Struct., 2008, 883, 195.
34. K. Yoshida, S. Daigoku, et al., J. Chem. Phys., 2003, 119, 6132.
35. S. Kuprin, A. Graslund and A. Ehrenberg, Biochem. Biophys. Res. Commun., 1995, 217, 1151.
36. Y. Mizutani, et al., J. Phys. Chem., 1991, 95, 1790.
37. J.-P. Bégué, D. Bonnet-Delpon and B. Crousse, Synlett, 2004, 18.
38. F. A. Davis, S. Chattopadhyay, J. C. Towson, S. Lal and T. Reddy, J. Org. Chem., 1988, 53, 2087.
39. For the first disclosure of a catalytic oxidation (sulfide to sulfoxide) mediated by an oxaziridine oxidant, see: F. A. Davis, S. G. Lal and H. D. Durst, J. Org. Chem., 1988, 53, 5004.
40. R. Mello, L. Cassidei and M. Fiorentino, J. Am. Chem. Soc., 1991, 113, 2205.
41. A. L. Baumstark, F. Kovac and P. C. Vasquez, Can. J. Chem., 1999, 77, 308.
42. Reactions with electron neutral or electron rich arenes yield a mixture of products, presumed to result from oxidation of the aromatic ring. Similar results are obtained with dioxiranes, see: A. Altamura, et al., Tetrahedron Lett., 1991, 32, 5445.
43. E. Mincione, T. Prencipe and R. Curci, J. Org. Chem., 1992, 57, 2182.
44. M. E. González-Núñez, R. Mello, A. Olmos and G. Asensio, J. Org. Chem., 2005, 70, 10879.
45. R. J. Kennedy and A. M. Stock, J. Org. Chem., 1960, 25, 1901.
46. B. De Poorter, M. Ricci and B. Meunier, Tetrahedron Lett., 1985, 26, 4459.