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Synlett 2014; 25(10): 1458-1460
DOI: 10.1055/s-0033-1341243
DOI: 10.1055/s-0033-1341243
letter
Copper-Catalyzed Aerobic Oxidative C–C Bond Cleavage of 1,3-Diaryldiketones To Synthesize 1,2-Diketones
Further Information
Publication History
Received: 12 February 2014
Accepted after revision: 25 March 2014
Publication Date:
08 May 2014 (online)
Abstract
An aerobic oxidative C–C bond cleavage of 1,3-diaryldiketones for the synthesis of 1,2-diketones by using O2 as the oxidant has been developed. Control experiments illustrate that the copper catalyst not only assist the aerobic oxidative process of 1,3-diketones, but also catalyze the 1,2-Wagner–Meerwein-type rearrangement process.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
-
References and Notes
- 1a Ita BI, Offiong OE. Mater. Chem. Phys. 2001; 70: 330
- 1b Husar B, Commereuc S, Lukac I, Chmela S, Nedelec JM, Baba M. J. Phys. Chem. B 2006; 110: 5315
- 1c Corrales T, Catalina F, Peinado C, Allen NS. J. Photochem. Photobiol. A 2003; 159: 103
- 2a Deng X, Mani N. Org. Lett. 2006; 8: 269
- 2b Shipe WD, Yang F, Zhao Z, Wolkenberg SE, Nolt MB, Lindsley CW. Heterocycles 2006; 70: 655
- 2c Held I, Xu SJ, Zipse H. Synthesis 2007; 1185
- 2d Boyce GR, Johnson JS. Angew. Chem. Int. Ed. 2010; 49: 8930
- 2e Rong F, Chow S, Yan S, Larson G, Hong Z, Wu J. Bioorg. Med. Chem. Lett. 2007; 17: 1663
- 2f McKenna JM, Halley F, Souness JE, McLay IM, Pickett SD, Collis AJ, Page K, Ahmed I. J. Med. Chem. 2002; 45: 2173
- 2g Singh SK, Saibaba V, Ravikumar V, Rudrawar SV, Daga P, Rao CS, Akhila V, Hegde P, Rao YK. Bioorg. Med. Chem. 2004; 12: 1881
- 3a Cornell CN, Sigman MS. Inorg. Chem. 2007; 46: 1903
- 3b Kotov V, Scarborough CC, Stahl SS. Inorg. Chem. 2007; 46: 1910
- 3c Keith JA, Henry PM. Angew. Chem. Int. Ed. 2009; 48: 9038
- 3d Ren W, Xia Y, Ji S.-J, Zhang Y, Wan X, Zhao J. Org. Lett. 2009; 11: 1841
- 3e Chen S, Liu Z, Shi E, Chen L, Wei W, Li H, Cheng Y, Wan X. Org. Lett. 2011; 13: 2274
- 3f Ren W, Liu J, Chen L, Wan X. Adv. Synth. Catal. 2010; 352: 1424
- 3g Mori S, Takubo M, Yanase T, Maegawa T, Monguchi Y, Sajiki H. Adv. Synth. Catal. 2010; 352: 1630
- 4a Okimoto M, Takahashi Y, Nagata Y, Sasaki G, Numata K. Synthesis 2005; 705
- 4b Joo C, Kang S, Kim SM, Han H, Yang JW. Tetrahedron Lett. 2010; 51: 6006
- 4c Alamsetti SK, Mannam S, Mutupandi P, Sekar G. Chem. Eur. J. 2009; 15: 1086
- 4d Qi C, Jiang H, Huang L, Chen Z, Chen H. Synthesis 2011; 387
- 5a Tada N, Shomura M, Nakayama H, Miura T, Itoh A. Synlett 2010; 1979
- 5b Karlsson I, Hillerstrom L, Stenfeldt A.-L, Martensson J, Borje A. Chem. Res. Toxicol. 2009; 22: 1881
- 5c Kim SS, Mah YJ, Kim AR, Cho KW. J. Photosci. 2004; 11: 129
- 5d Shimakawa Y, Morikawa T, Sakaguchi S. Tetrahedron Lett. 2010; 51: 1786
- 5e Suzuki Y, Bakar A, Tanoi T, Nomura N, Sato M. Tetrahedron 2011; 67: 4710
- 6 Huang LH, Cheng K, Yao BB, Xie YJ, Zhang YH. J. Org. Chem. 2011; 76: 5732
- 7 Yuan Y, Zhu H. Eur. J. Org. Chem. 2012; 329
- 8a Wendlandt AE, Suess AM, Stahl SS. Angew. Chem. Int. Ed. 2011; 50: 11062
- 8b Zhang C, Tang C, Jiao N. Chem. Soc. Rev. 2012; 41: 3464
- 8c Campbell AN, Stahl SS. Acc. Chem. Res. 2012; 45: 851
- 9a Wang H, Wang Y, Liang D, Liu L, Zhang J, Zhu Q. Angew. Chem. Int. Ed. 2011; 50: 5678
- 9b Wang J, Wang J, Zhu Y, Lu P, Wang Y. Chem. Commun. 2011; 47: 3275
- 9c Hausser A, Trautmann M, Roduner E. Chem. Commun. 2011; 47: 6954
- 9d Zhang C, Zhang L, Jiao N. Adv. Synth. Catal. 2012; 354: 1293
- 9e Liu Q, Wu P, Yang Y, Zeng Z, Liu J, Yi H, Lei A. Angew. Chem. Int. Ed. 2012; 51: 4666
- 9f Xu Z, Zhang C, Jiao N. Angew. Chem. Int. Ed. 2012; 51: 11367
- 9g Li X, Huang L, Chen H, Wu W, Huang H, Jiang H. Chem. Sci. 2012; 3: 3463
- 9h Du F.-T, Ji J.-X. Chem. Sci. 2012; 3: 460
- 9i Zhang C, Jiao N. Angew. Chem. Int. Ed. 2010; 49: 6174
- 9j Zhang C, Jiao N. J. Am. Chem. Soc. 2010; 132: 28
- 9k Zhang C, Xu Z, Zhang L, Jiao N. Angew. Chem. Int. Ed. 2011; 50: 11088
- 9l Zhang C, Jiao N. Org. Chem. Front. 2014; 1: 109
- 10 Typical Procedure A reaction mixture of CuBr (3.6 mg, 0.025 mmol), pyridine (10.0 mg, 0.125 mmol), 1,3-diphenylpropane-1,3-dione 1a (56.1 mg, 0.25 mmol) in toluene (2 mL) under O2 (1 atm) was stirred at 100 °C for 24 h. After being cooled to r.t. and concentrated under vacuum, the residue was purified by flash chromatography on a short silica gel (eluent: PE–EtOAc, 40:1) to afford 27 mg (51%) of 2a.
- 11 Zhang C, Feng P, Jiao N. J. Am. Chem. Soc. 2013; 135: 15257
- 12 Barbiero G, Kim W.-G, Hay AS. Tetrahedron Lett. 1994; 35: 5833
- 13 Roberts JD, Smith DR, Lee CC. J. Am. Chem. Soc. 1951; 73: 618
For some selected reviews about copper-catalyzed aerobic oxidative dehydrogenative coupling reaction in the last three years, see:
For some selected examples about copper-catalyzed aerobic oxidative dehydrogenative coupling reaction in the last three years, see: