Synthesis 2014; 46(14): 1853-1858
DOI: 10.1055/s-0033-1339109
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis of α-Ketoamides from Aryl Methyl Ketones and N,N-Dimethylformamide via Copper-Catalyzed Aerobic Oxidative Coupling

Mingxin Zhou
Institute of Next Generation Matter Transformation, College of Chemical Engineering at Huaqiao University, 668 Jimei Blvd, Xiamen, Fujian 361021, P. R. of China   Email: qsong@hqu.edu.cn
,
Qiuling Song*
Institute of Next Generation Matter Transformation, College of Chemical Engineering at Huaqiao University, 668 Jimei Blvd, Xiamen, Fujian 361021, P. R. of China   Email: qsong@hqu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 23 February 2014

Accepted after revision: 13 April 2014

Publication Date:
28 May 2014 (online)

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

 
  • 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
    • 6a Muzart J. Tetrahedron 2009; 65: 8313
    • 6b Ding S, Jiao N. Angew. Chem. Int. Ed. 2012; 51: 9226
    • 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