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Synthesis 2013; 45(5): 615-620
DOI: 10.1055/s-0032-1318172
DOI: 10.1055/s-0032-1318172
paper
Co(acac)2-Catalyzed Allylic and Benzylic Oxidation by tert-Butyl Hydroperoxide
Further Information
Publication History
Received: 19 November 2012
Accepted after revision: 18 January 2013
Publication Date:
01 February 2013 (online)
Abstract
Various allylic and benzylic substrates were oxidized to the corresponding enones, arenealdehydes and aryl ketones in good yields with tert-butyl hydroperoxide in the presence of catalytic amounts of Co(acac)2 under mild conditions. The reactivity, selectivity, and scope of the reaction were investigated.
Key words
Co(acac)2 - allylic and benzylic oxidation - tert-butyl hydroperoxide - enones - benzaldehydes - ketonesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Muzart J. Bull. Soc. Chim. Fr. 1986; 65
- 1b Page PC. B, McCarthy TJ. Comprehensive Organic Synthesis . Vol. 7. Trost BM, Flemming I. Pergamon; Oxford: 1991: 83-117
- 1c Sheldon RA, Kochi JK. Metal-Catalyzed Oxidations of Organic Compounds . Academic; New York: 1981
- 2a Marshall CW, Ray RE, Laos I, Riegel B. J. Am. Chem. Soc. 1957; 79: 6308
- 2b Dauben WG, Lorber M, Fullerton DS. J. Org. Chem. 1969; 34: 3587
- 2c Fullerton DS, Chen CM. Synth. Commun. 1976; 6: 217
-
2d Salmond WG, Barta MA, Havens JL. J. Org. Chem. 1978; 43: 2057
- 2e Rangarajan R, Eisenbraum EJ. J. Org. Chem. 1985; 50: 2435
- 2f Pearson AJ, Han GR. J. Org. Chem. 1985; 50: 2791
- 2g Rathore R, Saxena N, Chandrasekaran S. Synth. Commun. 1986; 16: 1493
- 2h Muzart J. Tetrahedron Lett. 1986; 27: 3139
- 2i Parish EJ, Chitrakorn S, Wei TY. Synth. Commun. 1986; 16: 1371
- 2j Parish EJ, Wei TY. Synth. Commun. 1987; 17: 1227
- 2k Chidambaram N, Chandrasekaran S. J. Org. Chem. 1987; 52: 5048
- 2l Muzart J. Tetrahedron Lett. 1987; 28: 2131
- 2m Amann A, Ourisson G, Luu B. Synthesis 1987; 1002
- 2n Choudary BM, Prasad AD, Bhuma V, Swapna V. J. Org. Chem. 1992; 57: 5841
- 2o Parish EJ, Sun H, Kizito SA. J. Chem. Res., Synop. 1996; 544
- 2p Das TK, Chaudhari K, Nandanan E, Chandwadkar AJ, Sudalai A, Ravindranathan T, Sivasanker S. Tetrahedron Lett. 1997; 38: 3631
- 2q Rothenberg G, Wiener H, Sasson Y. J. Mol. Catal. A: Chem. 1998; 136: 253
- 2r Bora U, Chaudhuri MK, Dey D, Kalita D, Kharmawphlang W, Mandal GC. Tetrahedron 2001; 57: 2445
- 3a Gannon SM, Krause JG. Synthesis 1987; 915
- 3b Li WS, Liu LK. Synthesis 1989; 293
- 3c Zhao D, Lee DG. Synthesis 1994; 915
- 3d Shaabani A, Lee DG. Tetrahedron Lett. 2001; 42: 5833
- 3e Pan JF, Chen K. J. Mol. Catal. A: Chem. 2001; 176: 19
- 4a Lee NH, Lee CS, Jung DS. Tetrahedron Lett. 1998; 39: 1385
- 4b Shing TK. M, Yeung YY, Su PL. Org. Lett. 2006; 8: 3149
- 5 Nagano T, Kobayashi S. Chem. Lett. 2008; 37: 1042
- 6a Salvador JA. R, Melo ML. S, Neves AS. C. Tetrahedron Lett. 1997; 38: 119
- 6b Li YC, Lee TB, Wang TY, Gamble AV, Gorden AE. V. J. Org. Chem. 2012; 77: 4628
- 7a Murahashi S, Oda Y, Naota T, Kuwabara T. Tetrahedron Lett. 1993; 34: 1299
- 7b Nikalje MD, Sudalai A. Tetrahedron 1999; 55: 5903
- 7c Yi CS, Kwon KH, Lee DW. Org. Lett. 2009; 11: 1567
- 7d Shingate BB, Hazra BG, Salunke DB, Pore VS. Tetrahedron Lett. 2011; 52: 6007
- 8a Yin XQ, Zhu ZY, Yang HW, Chen X, Zhao MY. Flavour Fragrance Cosmetics 2010; 1: 9
- 8b Chen Y, Yin DL, Zhong WZ, Mao LQ, Wang JH. Chin. J. Catal. 2006; 11: 983
- 9 Catino AJ, Nichols JM, Choi H, Gottipamula S, Doyle MP. Org. Lett. 2005; 7: 5167
- 10a Yu JQ, Corey EJ. Org. Lett. 2002; 4: 2727
- 10b Yu JQ, Corey EJ. J. Am. Chem. Soc. 2003; 125: 3232
- 10c Yu JQ, Wu HC, Corey EJ. Org. Lett. 2005; 7: 1415
- 11 Peng H, Lin AJ, Zhang Y, Jiang HL, Zhou JC, Cheng YX, Zhu CJ, Hu HW. ACS Catal. 2012; 2: 163
- 12 Li H, Li Z, Shi Z. Tetrahedron 2009; 65: 1856
- 13a Ishii Y, Nakayama K, Takeno M, Sakaguchi S, Iwahama T, Nishiyama Y. J. Org. Chem. 1995; 60: 3934
- 13b Yang G, Zhang Q, Miao H, Tong X, Xu J. Org. Lett. 2005; 7: 263
- 14 Silvestre AM, Salvador JA. R. Tetrahedron 2007; 63: 2439
- 15 Marwah P, Marwah A, Lardy HA. Green Chem. 2004; 6: 570
- 16 Zhao Y, Yeung YY. Org. Lett. 2010; 12: 2128
- 17 Murphy EF, Baiker A. J. Mol. Catal. A: Chem. 2002; 179: 233
- 18 Moriyama K, Takemura M, Togo H. Org. Lett. 2012; 14: 2414
- 19a Mahammad T, Shaikh A, Emmanuvel L, Sudalai A. J. Org. Chem. 2006; 71: 5043
- 19b Dohi T, Takenaga N, Goto A, Fujioka H, Kita Y. J. Org. Chem. 2008; 73: 7365
- 19c Ojha LR, Kudugunti S, Maddukuri PP, Kommareddy A, Gunna MR, Dokuparthi P, Gottam HB, Botha KK, Parapati DR, Vinod TK. Synlett 2009; 117
- 20a Gosmini C, Begouin JM, Moncomble A. Chem. Commun. 2008; 3221
- 20b Begouin JM, Gosmini C. J. Org. Chem. 2009; 74: 3221
- 20c Cahiez G, Chaboche C, Duplais C, Moyeux A. Org. Lett. 2009; 11: 277
- 20d Amatore M, Gosmini C. Chem. Commun. 2008; 5019
- 20e Hamaguchi H, Uemura M, Yasui H, Yorimitsu H, Oshima K. Chem. Lett. 2008; 1178
- 21a Salvador JA. R, Clark J. Chem. Commun. 2001; 33
- 21b Salvador JA. R, Clark J. Green Chem. 2002; 4: 352
- 21c Gonzalez MJ, Sullivan AC, Wilson JR. H. Tetrahedron Lett. 2003; 44: 4283
- 21d Modica E, Bombieri G, Colombo D, Marchini N, Ronchetti F, Scala A, Toma L. Eur. J. Org. Chem. 2003; 2964
- 21e Jin C, Zhang L, Su W. Synlett 2011; 1435
- 21f Maikap GC, Guhathakura D, Iqbal J. Synlett 1995; 189
- 21g Iyer S, Varghese JP. Synth. Commun. 1995; 25: 2261
- 22 Sodhi RK, Paul S, Clark JH. Green Chem. 2012; 14: 1649
- 23 Farzaneh F, Jalalian M, Tayebi L. E-J. Chem. 2012; 9: 2205 ; http://www.hindawi.com/journals/chem/
- 24a Piette Y, Debuigne A, Jerome C, Bodart V, Poli R, Detrembleur C. Polym. Chem. 2012; 3: 2880
- 24b Buchmeiser MR, Marino MG. Macromol. Mater. Eng. 2012; 297: 894
- 24c Semsarzadeh MA, Amiri S. J. Chem. Sci. 2012; 124: 521
- 24d Rene-Ponce Nze, Colombani O, Nicol E. J. Polm. Sci., Part A: Polym. Chem. 2012; 50: 4046
- 25 Takahashi S, Oritani T, Yamashita K. Agric. Biol. Chem. 1987; 51: 1143
- 26 Kim BT, Min YK, Asami T, Park NK, Jeong IH, Cho KY, Yoshida S. Bioorg. Med. Chem. Lett. 1995; 5: 275
- 27 Nyangulu JM, Nelson KM, Ros PA, Gai Y, Loewen M, Lougheed B, Quail JW, Culter AJ, Abrams SR. Org. Biomol. Chem. 2006; 4: 1400
- 28 Isler O, Lindlar H, Montavon M, Ruegg R, Saucy G, Zeller P. Helv. Chim. Acta 1956; 39: 2041
- 29 Takahashi S, Oritani T, Yamashita K. Agric. Biol. Chem. 1989; 53: 2711
- 30 Takahashi S, Oritani T, Yamashita K. Agric. Biol. Chem. 1988; 52: 297
- 31 Oelschlaegel S, Pieper L, Staufenbiel R, Gruner M, Zeippert L, Pieper B, Koelling-Speer I, Speer K. J. Agric. Food Chem. 2012; 60: 11811
- 32 Guirado A, Moss GP, Utley JH. P. Chem. Commun. 1987; 41
- 33 Tanaka M. Synthesis 1981; 47
- 34 Ohta S, Tachi T, Okamoto M. Synthesis 1983; 291
- 35 Ohta S, Okamoto M. Synthesis 1982; 756
- 36 Sivasubramanian K, Kaanumalle LS, Uppili S, Ramamurthy V. Org. Biomol. Chem. 2007; 5: 1569
- 37 Wang YF, Zhao HB, Hu ZZ, Kimura M, Zhang ZQ, Peng L, Hiratsuka K. Synthesis 2011; 287
- 38 Katritzky AR, Brown SB. Synthesis 1978; 619
- 39 Sur B, Adak MM, Pathak T, Hazra B, Banerjee A. Synthesis 1985; 52
- 40 Balaghi SE, Safaei E, Rafiee M, Kowsari MH. Polyhedron 2012; 47: 94
- 41 Sahi S, Paul S. Green Chem. Lett. Rev. 2012; 5: 343
- 42 Walvoord RR, Berritt S, Kozlowski MC. Org. Lett. 2012; 14: 4086
- 43 Zhang Y, Zhang N, Tang Z.-R, Xu Y.-J. ACS Nano 2012; 6: 9777
- 44 Shirini F, Akbari-Dadamahaleh S, Mohammad-Khah A. J. Mol. Catal. A: Chem. 2012; 363-364: 10
- 45 Murray AT, Matton P, Fairhurst NW. G, John MP, Carbery DR. Org. Lett. 2012; 14: 3656