C-H activation/borylation/oxidation: A one-pot unified route to meta-substituted phenols bearing ortho-/para-directing groups

Journal of the American Chemical Society

Volumn 125, Issue 26, 2003, Pages 7792-7793

  Maleczka Jr , Robert E ^a   Shi, Feng ^a   Holmes, Daniel ^a   Smith III, Milton R ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE; CARBON; HYDROGEN; PHENOL DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; OXIDATION; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

BORANES; OXIDATION-REDUCTION; PHENOLS;

EID: 0037865459     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0349857     Document Type: Article

References (27)

1. Tyman, J. H. P. Synthetic and Natural Phenols; Elsevier: New York, 1996.
2. (a) Hanson, P.; Jones, J. R.; Taylor, A. B.; Walton, P. H.; Timms, A. W. J. Chem. Soc., Perkin Trans. 2 2002, 1135-1150.
3. (b) George, T.; Mabon, R.; Sweeney, G.; Sweeney, J. B.; Tavassoli, A. J. Chem. Soc., Perkin Trans. 1 2000, 2529-2574.
4. (c) Sweeney, J. B. Contemp. Org. Synth. 1997, 4, 435-453.
5. For more recent innovative approaches, see: (a) Hoarau, C.; Pettus, T. R. R. Synlett 2003, 127-137. (b) Guo, Z.; Schultz, A. G.; Antoulinakis, E. G. Org. Lett. 2001, 3, 1177-1180. (c) Marchueta, I.; Olivella, S.; Sola, L.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett. 2001, 3. 3197-3200. (d) Serra, S.; Fuganti, C.; Moro, A. J. Org. Chem. 2001, 66, 7883-7888. (e) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554. (f) Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247.
6. For more recent innovative approaches, see: (a) Hoarau, C.; Pettus, T. R. R. Synlett 2003, 127-137. (b) Guo, Z.; Schultz, A. G.; Antoulinakis, E. G. Org. Lett. 2001, 3, 1177-1180. (c) Marchueta, I.; Olivella, S.; Sola, L.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett. 2001, 3. 3197-3200. (d) Serra, S.; Fuganti, C.; Moro, A. J. Org. Chem. 2001, 66, 7883-7888. (e) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554. (f) Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247.
7. For more recent innovative approaches, see: (a) Hoarau, C.; Pettus, T. R. R. Synlett 2003, 127-137. (b) Guo, Z.; Schultz, A. G.; Antoulinakis, E. G. Org. Lett. 2001, 3, 1177-1180. (c) Marchueta, I.; Olivella, S.; Sola, L.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett. 2001, 3. 3197-3200. (d) Serra, S.; Fuganti, C.; Moro, A. J. Org. Chem. 2001, 66, 7883-7888. (e) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554. (f) Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247.
8. For more recent innovative approaches, see: (a) Hoarau, C.; Pettus, T. R. R. Synlett 2003, 127-137. (b) Guo, Z.; Schultz, A. G.; Antoulinakis, E. G. Org. Lett. 2001, 3, 1177-1180. (c) Marchueta, I.; Olivella, S.; Sola, L.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett. 2001, 3. 3197-3200. (d) Serra, S.; Fuganti, C.; Moro, A. J. Org. Chem. 2001, 66, 7883-7888. (e) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554. (f) Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247.
9. For more recent innovative approaches, see: (a) Hoarau, C.; Pettus, T. R. R. Synlett 2003, 127-137. (b) Guo, Z.; Schultz, A. G.; Antoulinakis, E. G. Org. Lett. 2001, 3, 1177-1180. (c) Marchueta, I.; Olivella, S.; Sola, L.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett. 2001, 3. 3197-3200. (d) Serra, S.; Fuganti, C.; Moro, A. J. Org. Chem. 2001, 66, 7883-7888. (e) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554. (f) Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247.
10. For more recent innovative approaches, see: (a) Hoarau, C.; Pettus, T. R. R. Synlett 2003, 127-137. (b) Guo, Z.; Schultz, A. G.; Antoulinakis, E. G. Org. Lett. 2001, 3, 1177-1180. (c) Marchueta, I.; Olivella, S.; Sola, L.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett. 2001, 3. 3197-3200. (d) Serra, S.; Fuganti, C.; Moro, A. J. Org. Chem. 2001, 66, 7883-7888. (e) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554. (f) Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247.
11. For an alternative approach, see: Keil, W.; Wedemeyer, K.; Evertz, W. Ger. Offen. DE 2344925, 1975.
12. Per SciFinder Scholar.
13. Höger, S.; Bonrad, K.; Mourran, A.; Beginn, U.; Möller, M. J. Am. Chem. Soc. 2001, 123, 5651-5659.
14. (a) Hodgson, H. H.; Wignall, J. S. J. Chem. Soc. 1926, 2077-2079.
15. (b) Kohn, M.; Zandman, A. Monatsh. Chem. 1926, 47, 357-377.
16. (a) Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III. Science 2002, 295, 305-308 and references cited therein.
17. (b) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390-391 and references cited therein.
18. Webb, K. S.; Levy, D. Tetrahedron Lett. 1995, 36, 5117-5118.
19. Interestingly, Webb and Levy (ref 9) reported that oxidations above 15 °C gave lower yields.
20. See Supporting Information (SI) for full details.
21. (a) Magdziak, D.; Rodriguez, A. A.; Van De Water, R. W.; Pettus, T. R. R. Org. Lett. 2002, 4, 285-288 and references cited therein.
22. (b) Crandall, J. K.; Zucco, M.; Kirsch, R. S.; Coppert, D. M. Tetrahedron Lett. 1991, 32. 5441-5444.
23. Preliminary spectroscopic studies suggest that transient amounts of N-oxides are being formed during these reactions. Further analyses of this process are ongoing and will be reported elsewhere.
24. Demethylation of 2,6-dichloroanisole is known to be facile. See Majetich, G.; Zhang, Y.; Wheless, K. Tetrahedron Lett. 1994, 47, 8727-8730.
25. We have not ruled out in situ formation of DMDO when acetone is the solvent. However, our reactions are run in the absence of base or buffer, which are typically added to promote DMDO formation. See ref 9 and Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. Furthermore, a reaction using DMDO in place of aq Oxone only afforded a trace of the phenol.
26. 2.
27. Ishiyama, T.; Takagi, J.; Hartwig, J. F.; Miyaura, N. Angew. Chem., Int. Ed. 2002, 41, 3056-3058.