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Synthesis 2014; 46(14): 1853-1858
DOI: 10.1055/s-0033-1339109
DOI: 10.1055/s-0033-1339109
special topic
Synthesis of α-Ketoamides from Aryl Methyl Ketones and N,N-Dimethylformamide via Copper-Catalyzed Aerobic Oxidative Coupling
Further Information
Publication History
Received: 23 February 2014
Accepted after revision: 13 April 2014
Publication Date:
28 May 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201414/lookinside/thumbnails/10.1055-s-0033-1339109-1.jpg)
Abstract
A copper-catalyzed aerobic oxidative coupling of aryl methyl ketones with N,N-dimethylformamide was developed, which afforded α-ketoamides by a sequence of dioxygen activation, C–H bond functionalization, and amide formation with N,N-dimethylformamide as the nitrogen source. Molecular oxygen was found to play a crucial role in this transformation.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
References
- 1a Fusetani N, Matsunaga S, Matsumoto H, Takebayashi Y. J. Am. Chem. Soc. 1990; 112: 7053
- 1b Hagihara M, Schreiber SL. J. Am. Chem. Soc. 1992; 114: 6570
- 1c Maryanoff BE, Greco MN, Zhang H.-C, Andrade-Gordon P, Kauffman JA, Nicolaou KC, Liu A, Brungs PH. J. Am. Chem. Soc. 1995; 117: 1225
- 1d Li Z, Ortega-Vilain A.-C, Patil GS, Chu D.-L, Foreman JE, Eveleth DD, Powers JC. J. Med. Chem. 1996; 39: 4089
- 1e Muldoon J, Brown SN. Org. Lett. 2002; 4: 1043
- 1f Holenz J, Mercè R, Díaz JL, Guitart X, Codony X, Dordal A, Romero G, Torrens A, Mas J, Andaluz B, Hernández S, Monroy X, Sánchez E, Hernández E, Pérez R, Cubí R, Sanfeliu O, Buschmann H. J. Med. Chem. 2004; 48: 1781
- 1g Chen Y.-H, Zhang Y.-H, Zhang H.-J, Liu D.-Z, Gu M, Li J.-Y, Wu F, Zhu X.-Z, Li J, Nan F.-J. J. Med. Chem. 2006; 49: 1613
- 2a Jesuraj JL, Sivaguru J. Chem. Commun. 2010; 46: 4791
- 2b Zhang Z, Zhang Q, Ni Z, Liu Q. Chem. Commun. 2010; 46: 1269
- 2c Tomita D, Yamatsugu K, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2009; 131: 6946
- 2d Yang L, Wang D.-X, Huang Z.-T, Wang M.-X. J. Am. Chem. Soc. 2009; 131: 10390
- 3a Singh RP, Shreeve JN. M. J. Org. Chem. 2003; 68: 6063
- 3b Heaney F, Fenlon J, McArdle P, Cunningham D. Org. Biomol. Chem. 2003; 1: 1122
- 3c Zhang C, Zong X, Zhang L, Jiao N. Org. Lett. 2012; 14: 3280
- 3d Lamani M, Prabhu KR. Chem. Eur. J. 2012; 18: 14638
- 3e Zhang X, Yang W, Wang L. Org. Biomol. Chem. 2013; 11: 3649
- 3f Wei W, Shao Y, Hu H, Zhang F, Zhang C, Xu Y, Wan X. J. Org. Chem. 2012; 77: 7157
- 3g Mupparapu N, Khan S, Battula S, Kushwaha M, Gupta AP, Ahmed QN, Vishwakarma RA. Org. Lett. 2014; 16: 1152
- 4a Zhang C, Jiao N. J. Am. Chem. Soc. 2009; 132: 28
- 4b Zhang C, Xu Z, Zhang L, Jiao N. Angew. Chem. Int. Ed. 2011; 50: 11088
- 4c Du F.-T, Ji J.-X. Chem. Sci. 2012; 3: 460
- 4d Lamani M, Prabhu KR. Chem. Eur. J. 2012; 18: 14638
-
5a Liu J, Zhang R, Wang S, Sun W, Xia C. Org. Lett. 2009; 11: 1321
- 5b Iizuka M, Kondo Y. Chem. Commun. 2006; 1739
- 5c Murphy ER, Martinelli JR, Zaborenko N, Buchwald SL, Jensen KF. Angew. Chem. Int. Ed. 2007; 46: 1734
- 5d Fukuyama T, Nishitani S, Inouye T, Morimoto K, Ryu I. Org. Lett. 2006; 8: 1383
- 7a Zhu Y.-P, Lian M, Jia F.-C, Liu M.-C, Yuan J.-J, Gao Q.-H, Wu A.-X. Chem. Commun. 2012; 48: 9086
- 7b Evans RW, Zbieg JR, Zhu S, Li W, MacMillan DW. C. J. Am. Chem. Soc. 2013; 135: 16074
- 8 Zhao Q, Miao T, Zhang X, Zhou W, Wang L. Org. Biomol. Chem. 2013; 11: 1867
- 9a Song Q, Feng Q, Zhou M. Org. Lett. 2013; 15: 5990
- 9b Song Q, Feng Q, Yang K. Org. Lett. 2014; 16: 624
- 9c Feng Q, Song Q. J. Org. Chem. 2014; 79: 1867
- 9d Feng Q, Song Q. Adv. Synth. Catal. 2014; 356 in press; DOI: 10.1002/adsc.201301001
- 10 Wang H, Guo L.-N, Duan X.-H. Org. Biomol. Chem. 2013; 11: 4573
- 11 Li D, Wang M, Liu J, Zhao Q, Wang L. Chem. Commun. 2013; 49: 3640