Efficient synthesis of p-quinols using catalytic hypervalent iodine oxidation of 4-arylphenols with 4-iodophenoxyacetic acid and oxone®

Chemical and Pharmaceutical Bulletin

Volumn 57, Issue 6, 2009, Pages 643-645

  Yakura, Takayuki ^a   Omoto, Masanori ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

4 arylphenol; 4 iodophenoxyacetic acid; Catalytic hypervalent iodine oxidation; Oxone ; p quinol

Indexed keywords

4 IODOPHENOXYACETIC ACID; 4 QUINOLONE DERIVATIVE; ACETIC ACID DERIVATIVE; DIOXANE; IODINE; PHENOL DERIVATIVE; SODIUM PEROXIDE; TETRAHYDROFURAN; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; OXIDATION; QUANTUM YIELD; REACTION TIME; SOLUBILITY;

CATALYSIS; HYDROQUINONES; INDICATORS AND REAGENTS; IODINE COMPOUNDS; IODOBENZENES; OXIDATION-REDUCTION; PHENOLS; SULFURIC ACIDS;

EID: 66949112198     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.57.643     Document Type: Article

References (58)

1. Wang X., Porco J. A. Jr., Angew. Chem. Int. Ed., 44, 3067-3071 (2005).
2. Soriente A., Rocca A. D., Sodano G., Trincone A., Tetrahedron, 53, 4693-4702 (1997).
3. Alcaraz L., Macdonald G., Ragot J. P., Lewis N., Taylor R. J. K., J. Org. Chem., 63, 3526-3527 (1998).
4. Ata A., Kerr R. G., Moya C. E., Jacobs R. S., Tetrahedron, 59, 4215-4222 (2003).
5. Wells G., Berry J. M., Bradshaw T. D., Burger A. M., Seaton A., Wang B., Westwell A. D., Stevens M. F. G., J. Med. Chem., 46, 532-541 (2003).
6. Berry J. M., Bradshaw T. D., Fichtner I., Ren R., Schwalbe C. H., Wells G., Chew E.-H., Stevens M. F. G., Westwell A. D., J. Med. Chem., 48, 639-644 (2005).
7. Lion C. J., Matthews C. S., Wells G., Bradshaw T. D., Stevens M. F. G., Westwell A. D., Bioorg. Med. Chem. Lett., 16, 5005-5008 (2006).
8. Milić D. R., Gašić M. J., Muster W., Csanádi J. J., Šolaja B. A., Tetrahedron, 53, 14073-14084 (1997).
9. Milić D. R., Kapor A., Markov B., Ribar B., Strümpel M., Juranić Z., Gašić M. J., Šolaja B. A., Molecules, 4, 338-352 (1999).
10. Magdziak D., Meek S. J., Pettus T. R. R., Chem. Rev., 104, 1383-1429 (2004).
11. Matsuura T., Omura K., Nakashima R., Bull. Chem. Soc. Jpn., 38, 1358-1362 (1965).
12. Adam W., Kiliç H., Saha-Möller C. R., Synlett, 2002, 510-512 (2002).
13. DeRosa M. C., Crutchley R. J., Coord. Chem. Rev., 233-234, 351-371 (2002).
14. Sels B. F., De Vos D. E., Jacobs P. A., Angew. Chem. Int. Ed., 44, 310-313 (2005).
15. Zilbeyaz K., Sahin E., Kilic H., Tetrahedron: Asymmetry, 18, 791-796 (2007).
16. Carreño M. C., González-López M., Urbano A., Angew. Chem. Int. Ed., 45, 2737-2741 (2006).
17. Barradas S., Carreño M. C., González-López M., Latorre A., Urbano A., Org. Lett., 9, 5019-5022 (2007).
18. Pelter A., Elgendy S. M. A., J. Chem. Soc., Perkin Trans. 1, 1993, 1891-1896 (1993).
19. Pitsinos E. N., Moutsos V. I., Vageli O., Tetrahedron Lett., 48, 1523-1526 (2007).
20. Lin A.-S., Nakagawa-Goto K., Chang F.-R., Yu D., Morris-Natschke S. L., Wu C.-C., Chen S.-L., Wu Y.-C., Lee K.-H., J. Med. Chem., 50, 3921-3927 (2007).
21. Vo N. T., Pace R. D. M., O'Hara F., Gaunt M. J., J. Am. Chem. Soc., 130, 404-405 (2008).
22. "Hypervalent Iodine in Organic Synthesis," ed. by Varvoglis A., Academic Press, San Diego, 1997.
23. Wirth T., Hirt U. H., Synthesis, 1999, 1271-1287 (1999).
24. Wirth T., Angew. Chem. Int. Ed., 40, 2812-2814 (2001).
25. Zhdankin V. V., Stang P. J., Chem. Rev., 102, 2523-2584 (2002).
26. Wirth T., Angew. Chem. Int. Ed., 44, 3656-3665 (2005).
27. Felpin F.-X., Tetrahedron Lett., 48, 409-412 (2007).
28. Yakura T., Konishi T., Synlett, 2007, 765-768 (2007).
29. Yakura T., Tian Y., Yamauchi Y., Omoto M., Konishi T., Chem. Pharm. Bull., 57, 252-256 (2009).
30. Marcotullio M. C., Epifano F., Curini M., Trends Org. Chem., 10, 21-34 (2003).
31. Yakura T., Yamauchi Y., Tian Y., Omoto M., Chem. Pharm. Bull., 56, 1632-1634 (2008).
32. Dohi T., Kita Y., Kagaku, 61, 68-69 (2006).
33. Richardson R. D., Wirth T., Angew. Chem. Int. Ed., 45, 4402-4404 (2006).
34. Ochiai M., Miyamoto K., Eur. J. Org. Chem., 2008, 4229-4239 (2008).
35. Dohi T., Maruyama A., Yoshimura M., Morimoto K., Tohma H., Kita Y., Angew. Chem. Int. Ed., 44, 6193-6196 (2005).
36. Ochiai M., Takeuchi Y., Katayama T., Sueda T., Miyamoto K., J. Am. Chem. Soc., 127, 12244-12245 (2005).
37. Yamamoto Y., Togo H., Synlett, 2006, 798-800 (2006).
38. Dohi T., Maruyama A., Minamitsuji Y., Takenaga N., Kita Y., Chem. Commun., 2007, 1224-1226 (2007).
39. Richardson R. D., Page T. K., Altermann S., Paradine S. M., French A. N., Wirth T., Synlett, 2007, 538-542 (2007).
40. Akiike J., Yamamoto Y., Togo H., Synlett, 2007, 2168-2172 (2007).
41. Yamamoto Y., Kawano Y., Toy P. H., Togo H., Tetrahedron, 63, 4680-4687 (2007).
42. Richardson R. D., Desaize M., Wirth T., Chem. Eur. J., 13, 6745-6754 (2007).
43. Moroda A., Togo H., Synthesis, 2008, 1257-1261 (2008).
44. Thottumkara A. P., Bowsher M. S., Vinod T. K., Org. Lett., 7, 2933-2936 (2005).
45. Schulze A., Giannis A., Synthesis, 2006, 257-260 (2006).
46. Typical reaction procedure for oxidation of 4-arylphenols 1: Compound 3 (0.050 mmol) was added to a solution of 1 (1.0 mmol) in THF-water (1:5, 6 ml), followed by Oxone® (4 mmol) at room temperature. After 1 was completely consumed, as indicated by TLC, the mixture was diluted with ethyl acetate and washed with water. The organic layer was then washed with aqueous saturated sodium bicarbonate solution and dried, concentrated. The residue was purified by column chromatography on silica gel to give pure 2. The alkaline solution was acidified by 10% hydrochloric acid solution and extracted with ethyl acetate. The organic layer was dried and concentrated to give recovered 3, which can be used after recrystallization from diethyl etherhexane. All new compounds gave satisfactory spectrospecific data.
47. Ranganathan S., Ranganathan D., Singh S., Bhattacharyya D., J. Chem. Soc., Chem. Commun., 1987, 1887-1888 (1987).
48. Magdziak D., Rodriguez A. A., Van De Water R. W., Pettus T. R. R., Org. Lett., 4, 285-288 (2002).
49. Quideau S., Pouységu L., Deffieux D., Ozanne A., Gagnepain J., Fabre I., Oxoby M., ARKIVOC, vi, 106-119 (2003).
50. Lebrasseur N., Gagnepain J., Ozanne-Beaudenon A., Léger J.-M., Quideau S., J. Org. Chem., 72, 6280-6283 (2007).
51. Frigerio M., Santagostino M., Sputore S., J. Org. Chem., 64, 4537-4538 (1999).
52. Mülbaier M., Giannis A., Angew. Chem. Int. Ed., 40, 4393-4394 (2001).
53. Mülbaier M., Giannis A., ARKIVOC, vi, 228-236 (2003).
54. Kim D.-K., Chung W.-J., Lee Y.-S., Synlett, 2005, 279-282 (2005).
55. Ladziata U., Willging J., Zhdankin V. V., Org. Lett., 8, 167-170 (2006).
56. Koposov A. Y., Litvinov D. N., Zhdankin V. V., Ferguson M. J., McDonald R., Tykwinski R. R., Eur. J. Org. Chem., 2006, 4791-4795 (2006).
57. Karimov R. R., Kazhkenov Z.-G. M., Modjewski M. J., Peterson E. M., Zhdankin V. V., J. Org. Chem., 72, 8149-8151 (2007).
58. 2O showed no presence of hypervalent iodine species.