Aerobic photocatalytic oxidation of activated benzylic and allylic alcohols to carbonyl compounds catalyzed by molecular iodine

Tetrahedron Letters

Volumn 47, Issue 50, 2006, Pages 8953-8957

  Farhadi, Saeid ^a   Zabardasti, Abedien ^a   Babazadeh, Zaynab ^a  

^a LORESTAN UNIVERSITY   (Iran)

Author keywords

Aerobic; Benzylic alcohols; Iodine; Oxidation; Photocatalytic

Indexed keywords

ACETONITRILE; ALCOHOL DERIVATIVE; ALDEHYDE; BENZYL DERIVATIVE; CARBONYL DERIVATIVE; HYDROXYL GROUP; IODINE; KETONE;

AEROBIC METABOLISM; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; OXIDATION KINETICS; PHOTOCATALYSIS; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 33750606538     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.036     Document Type: Article

References (55)

1. Hudlicky M. Oxidations in Organic Chemistry (1990), ACS, Washington, DC
2. Larock R.C. Comprehensive Organic Transformations. 2nd ed. (1999), Wiley-VCH, New York
3. Noyori R., and Hashigushi S. Acc. Chem. Res. 30 (1997) 97-102 and references cited therein
4. Zhan B.-Z., White M.A., Sham T.-K., Pincock J.A., Doucet R.J., Rao K.V.R., Robertson K.N., and Cameron T.S. J. Am. Chem. Soc. 125 (2003) 2195-2199
5. Ciriminna R., and Pagliaro M. Chem. Eur. J. 9 (2003) 5067-5073
6. Sheldon R.A., Arends I.W.C.E., ten Brink G.-J., and Dijksman A. Acc. Chem. Res. 35 (2002) 774-781
7. Ji H.-B., and Wang L.-F. Chin. J. Chem. 20 (2002) 944-950
8. Hasan M., Musawir M., Davey P.N., and Kozhevnikov I.V. J. Mol. Catal. A: Chem. 180 (2002) 77-84
9. Yamaguchi K., Mori K., Mizugaki T., Ebitani K., and Kaneda K. J. Am. Chem. Soc. 122 (2000) 7144-7145
10. Sheldon R.A., Arends I.W.C.E., and Dijksman A. Catal. Today 57 (2000) 157-166
11. Lee M., and Chang S. Tetrahedron Lett. 41 (2000) 7507-7510
12. Bleloch A., Johnson B.F.G., Ley S.V., Price A.J., Shephart D.S., and Thomas A.W. Chem. Commun. (1999) 1907-1908
13. Stahl S.S. Angew. Chem., Int. Ed. 43 (2004) 3400-3420 and references cited therein
14. Steinhoff B.A., Fix S.R., and Stahl S.S. J. Am. Chem. Soc. 124 (2002) 766-767
15. Stahl S.S., Thorman J.L., Nelson R.C., and Kozee M.A. J. Am. Chem. Soc. 123 (2001) 7188-7189
16. Peterson K.P., and Larock R.C. J. Org. Chem. 63 (1998) 3185-3189
17. Marko I.E., Giles P.R., Tsukazaki M., Brown S.M., and Urch C.J. Science 274 (1996) 2044-2046
18. Marko I.E., Giles P.R., Tsukazaki M., Chelle-Regnaut I., Gautier A., Brown S.M., and Urch C.J. J. Org. Chem. 64 (1999) 2433-2439
19. Marko I.E., Gautier A., Dumeunier R., Doda K., Philippart F., Brown S.M., and Urch C.J. Angew. Chem., Int. Ed. 43 (2004) 1588-1591
20. Adam W., Saha-Moller C.R., and Ganeshpure P.A. Chem. Rev. 101 (2001) 3499-3548
21. Murahashi S.-I., Naota T., and Hirai N. J. Org. Chem. 58 (1993) 7318-7319
22. For a review, see:. De Nooy A.E.J., Besemer A.C., and van Bekkum H. Synthesis (1996) 1153-1174
23. Anelli P.L., Biffi C., Montanari F., and Quici S. J. Org. Chem. 52 (1987) 2559-2562
24. Anelli P.L., Biffi C., Montanari F., and Quici S. J. Org. Chem. 54 (1989) 2970-2972
25. Anelli P.L., Montanari F., and Quici S. J. Org. Chem. 55 (1990) 212-219
26. Zhao M., Li J., Mano E., Song Z., Tschaen D.M., Grabowski E.J.J., and Reider P.J. J. Org. Chem. 64 (1999) 2564-2566
27. Inokuchi T., Matsumoto S., Nishiyama T., and Torii S. J. Org. Chem. 55 (1990) 462-466
28. Melvin F., McNeill A., Henderson P.J.F., and Herbert R.B. Tetrahedron Lett. 40 (1999) 1201-1202
29. Bolm C., Magnus A.S., and Hildebrand J.P. Org. Lett. 2 (2000) 1173-1175
30. Einhorn J., Einhorn C., Ratajczak F., and Pierre J.-L. J. Org. Chem. 61 (1996) 7452-7454
31. De Mico A., Margarita R., Parlanti L., Vescovi A., and Piancatelli G. J. Org. Chem. 62 (1997) 6974-6977
32. Epp J.B., and Widlanski T.S. J. Org. Chem. 64 (1999) 293-295
33. Cella J.A., McGrath J.P., Kelley J.A., El-Soukkarry O., and Hilpert L. J. Org. Chem. 42 (1977) 2077-2080
34. Ma Z., Huang Q., and Bobbitt J.M. J. Org. Chem. 58 (1993) 4837-4843
35. Rychnovsky S.D., and Vaidyanathan R. J. Org. Chem. 64 (1999) 310-312
36. De Luca L., Giacomelli G., and Porcheddu A. Org. Lett. 3 (2001) 3041-3043
37. De Luca L., Giacomelli G., Masala S., and Porcheddu A. J. Org. Chem. 68 (2003) 4999-5001
38. Miller R.A., and Hoerrner R.S. Org. Lett. 5 (2003) 285-287
39. Liu R., Liang X., Dong C., and Hu X. J. Am. Chem. Soc. 126 (2004) 4112-4113
40. Liu R., Dong C., Liang X., Wang X., and Hu X. J. Org. Chem. 70 (2005) 729-731
41. Horspool W.M., and Song P.S. CRC Handbook of Organic Photochemistry and Photobiology (1995), CRC Press, Boca Raton
42. Farhadi S., Afshari M., Maleki M., and Babazadeh Z. Tetrahedron Lett. 46 (2005) 8483-8486
43. Beebe T.R., Hensley V.L., Ng F.W., Neo R.A., and Scott D.J. J. Org. Chem. 50 (1985) 3015-3016 and references cited therein
44. Cotton F.A., Wilkinson G., Murillo C.A., and Bochmann M. Advanced Inorganic Chemistry. 6th ed. (1999), Wiley, New York p 564
45. Cecchetto A., Fantana F., Minisci F., and Recupero F. Tetrahedron Lett. 42 (2001) 6651-6653
46. Minisci F., Punta C., Recupero F., Fantana F., and Pedulli G.F. Chem. Commun. (2002) 688-689
47. Minisci F., Recupero F., Pedulli G.F., and Lucarini M. J. Mol. Catal. A: Chem. 204-205 (2003) 63-90
48. Minisci F., Recupero F., Cecchetto A., Gambaotti C., Punta C., Faletti R., Paganelli R., and Pedulli G.F. Eur. J. Org. Chem. (2004) 109-119
49. Annunziatini C., Gerini M.F., Lanzalunga O., and Lucarini M. J. Org. Chem. 69 (2004) 3431-3438
50. Moriarty R.M., Hu H., and Gupta S.C. Tetrahedron Lett. 22 (1981) 1283-1286
51. Sorg G., Mengel A., Jung G., and Rademann J. Angew. Chem., Int. Ed. 40 (2001) 4395-4397
52. Mulbaier M., and Giannis A. Angew. Chem., Int. Ed. 40 (2001) 4393-4394
53. Moore J.D., and Finney S.N. Org. Lett. 4 (2002) 3001-3003
54. Reed N.N., Delgado M., Hereford K., Clapham B., and Janda K.D. Bioorg. Med. Chem. Lett. 12 (2002) 2047-2049
55. Dictionary of Organic Compounds. 6th ed. (1996), Chapman-Hall, London