A New Method for the Benzylic Oxidation of Alkylarenes Catalyzed by Hypervalent Iodine(III)

Abstract

A convenient and simple procedure is described for the oxidation of the benzylic C–H moiety of alkylarenes to give the corresponding aryl ketones, using tert-butyl hydroperoxide and m-chloroperoxybenzoic acid in the presence of a catalytic amount of the hypervalent iodine reagent, (diacetoxyiodo)benzene. The reactions typically occur in good yields in 2,2,2-trifluoroethanol as the solvent and at room temperature.

Key words

benzylic oxidations - hypervalent iodine reagent - (diacetoxyiodo)benzene - ketones

• References

• 1a Sheldon RA, Kochi JK. Metal-Catalyzed Oxidations of Organic Compounds . Academic Press; New York: 1981
• 1b Recupero F, Punta C. Chem. Rev. 2007; 107: 3800
• 1c Handbook of C–H Transformations . Dyker D. Wiley-VCH; Weinheim: 2005
• 2 Hudlicky M. Oxidations in Organic Chemistry, ACS Monograph No. 186. American Chemical Society; Washington DC: 1990
• 3a Modern Oxidation Methods . Backvall JE. Wiley-VCH; Weinheim: 2004
• 3b Choudary B, Prasad AD, Bhuma V, Swapna V. J. Org. Chem. 1992; 57: 5841
• 3c Modica E, Bombieri G, Colombo D, Machini N, Ronchetti F, Scala A, Toma L. Eur. J. Org. Chem. 2003; 2964
• 3d Jin C, Zhang L, Su WK. Synlett 2011; 1435
• 3e Nikalje MD, Sudaldai A. Tetrahedron 1999; 55: 5903
• 3f Gupta M, Paul S, Gupta R, Loupy A. Tetrahedron Lett. 2005; 46: 4957
• 3g Bonvin Y, Callens E, Larrosa I, Henderson DA, Oldham J, Burton AJ, Barrett AG. M. Org. Lett. 2005; 7: 4549
• 3h Catino AJ, Nichols JM, Choi H, Gottipamula S, Doyle MP. Org. Lett. 2005; 7: 5167
• 3i Nakanishi M, Bolm C. Adv. Synth. Catal. 2007; 349: 861
• 4a Ochiai M, Ito T, Masaki Y, Shira M. J. Am. Chem. Soc. 1992; 114: 6269
• 4b Ochiai M, Ito T, Takahashi H, Nakanishi A, Toyonari M, Sueda T, Goto S, Shiro M. J. Am. Chem. Soc. 1996; 118: 7716
• 4c Nicolaou KC, Zhong YL, Baran PS. J. Am. Chem. Soc. 2001; 123: 3183
• 4d Nicolaou KC, Montagnon T, Baran PS, Zhong YL. J. Am. Chem. Soc. 2002; 124: 2245
• 4e Yusubov MS, Zagulyaeva AA, Zhdankin VV. Chem. Eur. J. 2009; 15: 11091
• 4f Dohi T, Takenaga N, Goto A, Fujioka H, Kita Y. J. Org. Chem. 2008; 73: 7365
• 5 Zhao Y, Yeung YY. Org. Lett. 2010; 12: 2128
• 6 Zhao Y, Yim WL, Tan CK, Yeung YY. Org. Lett. 2011; 13: 4308
• 7a Ochiai M, Takeuchi Y, Katayama T, Sueda T, Miyamoto K. J. Am. Chem. Soc. 2005; 127: 12244
• 7b Dohi T, Maruyama A, Yoshimura M, Morimoto K, Tohma H, Kita Y. Angew. Chem. Int. Ed. 2005; 44: 6193
• 7c Richardson RD, Wirth T. Angew. Chem. Int. Ed. 2006; 45: 4402
• 7d Dohi T, Minamitsuji Y, Maruyama A, Hirose S, Kita Y. Org. Lett. 2008; 10: 3559
• 7e Ochiai M. Chem. Rec. 2007; 7: 13
• 7f Uyanik M, Ishihara K. Chem. Commun. 2009; 2086
• 7g Dohi T, Kita Y. Chem. Commun. 2009; 2073
• 7h Liu H.-G, Tan C.-H. Tetrahedron Lett. 2007; 48: 8220
• 8 Xu Y, Hu JT, Yan J. Chin. Chem. Lett. 2012; 23: 891
• 9 Wiley H, Hobson PH. J. Am. Chem. Soc. 1949; 71: 2429
• 10 Campo MA, Larock RC. J. Org. Chem. 2002; 67: 5616
• 11 Okuma K, Nojima A, Matsunaga N, Shioji K. Org. Lett. 2009; 11: 169
• 12 Ghammamy S, Imanieh H, Mohammady MK, Mazareey M. Asian J. Chem. 2005; 17: 2137
• 13 Hudson BE, Hauser CR. J. Am. Chem. Soc. 1941; 63: 3163
• 14 Qian W, Jin E, Bao W, Zhang Y. Tetrahedron 2006; 62: 556
• 15 Cai M, Zheng G, Ding G. Green Chem. 2009; 11: 1687
• 16 Chichibabin AE, Kuindshi BM, Benevolenskii SV. Ber. Dtsch. Chem. Ges. 1925; 58B: 1580