Pd/C-catalyzed deoxygenation of phenol derivatives using mg metal and MeOH in the presence of NH4OAc

Organic Letters

Volumn 8, Issue 5, 2006, Pages 987-990

  Sajiki, Hironao ^a   Mori, Akinori ^a   Mizusaki, Tomoteru ^a   Ikawa, Takashi ^a   Maegawa, Tomohiro ^a   Hirota, Kosaku ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33644941189     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060045q     Document Type: Article

References (44)

1. (a) Okuda, T.; Yoshida, T.; Hatano, T. Planta Med. 1989, 55, 117.
2. (b) Akiyama, H.; Sakushima, J.; Taniuchi, S.; Kanda, T.; Yanagida, A.; Kojima, T.; Teshima, R.; Kobayashi, Y.; Goda, Y.; Toyoda, M. Biol. Pharm. Bull. 2000, 23, 1370.
3. Peterson, G. A.; Kunng, F.; McCallumg, J. S.; Wulff, W. D. Tetrahedron Lett. 1987, 28, 1381.
4. Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. 1998, 37, 2700.
5. (a) Severin, T.; Ipach, I. Synthesis 1973, 796.
6. (b) Konieczny, M.; Harvey, R. G. J. Org. Chem. 1979, 44, 4813.
7. Node, M.; Nishide, K.; Ohta, K.; Fujita, E. Tetrahedron Lett. 1982, 23, 689.
8. Sebök, P.; Timar, T.; Eszenyi, T.; Patonay, T. J. Org. Chem. 1994, 59, 6318 and references therein.
9. (a) Rottendorf, H.; Sternhell, S. Aust. J. Chem. 1963, 16, 647.
10. (b) Clauss, K.; Jensen, H. Angew. Chem., Int. Ed. Engl. 1973, 12, 918.
11. Lonsky, W.; Traitler, H.; Kratzl, K. J. Chem. Soc., Perkin Trans. 1 1975, 169.
12. Subramanian, L. R. Synthesis 1984, 481.
13. (e) Cacchi, S.; Ciattini, P. G.; Morera, E.; Orter, G. Tetrahedron Lett. 1986, 27, 5541.
14. (f) Chen, Q.-Y.; He, Y.-B.; Yang, Z.-Y. J. Chem. Soc., Chem. Commun. 1986, 1452.
15. (g) Cabri, W.; Bernardinis, S. D.; Francalanci, F.; Penco, S. J. Org. Chem. 1990, 55, 350.
16. (h) Saa, J. M.; Dopico, M.; Martorell, G.; Garcia-Raso, A. J. Org. Chem. 1990, 55, 991.
17. Sasaki, K.; Sakai, M.; Sakakibara, Y.; Takagi, K. Chem. Lett. 1991, 2017.
18. (j) Kotsuki, H.; Datta, P. K.; Hayakawa, H.; Suenaga, H. Synthesis 1995, 1348.
19. (k) Lipshutz, B. H.; Buzard, D. J.; Vivian, R. W. Tetrahedron Lett. 1999, 40, 6871-6874.
20. 2-catalyzed reductive deoxygenation methods of polymer supported aromatic sulfonates are reported as a quite useful tool for combinatorial chemistry, while a perfluorated linker, phosphine ligand, and heating conditions are required; see: (a) Pan, Y.; Holmes, C. P. Org. Lett. 2001, 3, 2769.
21. (b) Cammidge, A. N.; Ngaini, Z. Chem. Commun. 2004, 1914.
22. Revell, J. D.; Ganesan, A. Chem. Commun. 2004, 1916.
23. Vowinkel, E.; Wolff, C. Chem. Ber. 1974, 107, 907.
24. (a) Sartoretto, P. A.; Sowa, F. J. J. Am. Chem. Soc. 1937, 59, 603.
25. (b) Sawa, Y. K.; Tsuji, N.; Maeda, S. Tetrahedron 1961, 15, 144 and 154.
26. Pirkle, W. H.; Zabriskie, J. L. J. Org. Chem. 1964, 29, 3124.
27. (a) Musliner, W. J.; Gates, J. W., Jr. J. Am. Chem. Soc. 1966, 88, 4271.
28. (b) Hussey, J.; Johnstone, R. A. Q. Tetrahedron 1982, 38, 3775.
29. (a) Pelletier, S. W.; Locke, D. M. J. Org. Chem. 1958, 23, 131.
30. (b) Kenner, G. W.; Williams, N. R. J. Chem. Soc. 1955, 522.
31. Goldkamo, A. H.; Hoehn, W. M.; Mikulec, R. A.; Nutting, E. F.; Cook, D. L. J. Med. Chem. 1965, 8, 409.
32. Rossi, R. A.; Bunnett, J. F. J. Org. Chem. 1973, 38, 2314.
33. (e) Shafer, S. J.; Closson, W. D.; van Dijk, J. M. F.; Piepers, O.; Buck, H. M. J. Am. Chem. Soc. 1977, 99, 5118.
34. (f) Dominianni, S. J.; Ryan, C. W.; DeArmitt, C. W. J. Org. Chem. 1977, 42, 344.
35. (g) Welch, S. C.; Walters, M. E. J. Org. Chem. 1978, 43, 4797.
36. (h) Shono, T.; Matsumura, Y.; Tsubata, K.; Sugihara, Y. J. Org. Chem. 1979, 44, 4508.
37. Recently, a practical and convenient synthetic method of preparing aryl triflates under aqueous conditions was reported by Merck's research group; see: Frantz, D. E.; Weaver, D. G.; Carey, J. P.; Kress, M. H.; Dolling, U. H. Org. Lett. 2002, 4, 4717.
38. (a) A selective reduction method of conjugated multiple bonds by excess amount of Mg metal-MeOH has been well-known, see: Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999; p 13.
39. (b) Olah et al. reported a Pd/C-catalyzed reduction of nonconjugated multiple bonds with 5 equiv of Mg metal-MeOH; see: Olah, G. A.; Prakash, G. K. S.; Arranaghi, M.; Bruce, M. R. Angew. Chem., Int. Ed. 1981, 20, 92.
40. Mg turnings for a Grignard reaction can be used without any pretreatment.
41. 3-catalyzed reduction of aryl triflates with Zn powder although such pioneering method required phosphine ligands and unstable in situ generated Ni(0) complex as a catalyst.
42. 4OAc toward the monoalkylation method of amines using nitriles as an alkylating agent; see: Sajiki, H.; Ikawa, T.; Hirota, K. Org. Lett. 2004, 6, 4977.
43. Formation of a small amount (6% in each case) of the homocoupling product (3) was also observed.
44. 4, filtered, and concentrated under reduced pressure.