Synthesis 2015; 47(05): 726-736
DOI: 10.1055/s-0034-1379975
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed One-Pot Synthesis of α-Ketoamides from 1-Arylethanols

Nidhi Sharma
Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu 600 036, India   eMail: gsekar@iitm.ac.in
,
Surya Srinivas Kotha
Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu 600 036, India   eMail: gsekar@iitm.ac.in
,
Nabajit Lahiri
Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu 600 036, India   eMail: gsekar@iitm.ac.in
,
Govindasamy Sekar*
Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu 600 036, India   eMail: gsekar@iitm.ac.in
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 14. November 2014

Accepted after revision: 15. Dezember 2014

Publikationsdatum:
28. Januar 2015 (online)


Abstract

A copper-catalyzed one-pot strategy for the synthesis of α-ketoamides from 1-arylethanols is described. This triple oxidation of 1-arylethanols involves alcohol oxidation, sp3 C–H oxidation, and oxidative amidation with amines. The protocol is highly efficient, delivering α-ketoamides in good to excellent yields.

Supporting Information

 
  • References

    • 1a Barrett DG, Catalano JG, Deaton DN, Hassell AM, Long ST, Miller AB, Miller LR, Ray JA, Samano V, Shewchuk LM, Wells-Knecht KJ, Willard DH, Wright LL. Bioorg. Med. Chem. Lett. 2006; 16: 1735
    • 1b Munoz B, Giam C.-Z, Wong C.-H. Bioorg. Med. Chem. 1994; 2: 1085
    • 1c Deng H, Jung J.-K, Liu T, Kuntz KW, Snapper ML, Hoveyda AH. J. Am. Chem. Soc. 2003; 125: 9032
    • 1d Sheha MM, Mahfouz NM, Hassan HY, Youssef AF, Mimoto T, Kiso Y. Eur. J. Med. Chem. 2000; 35: 887
    • 1e Knust H, Nettekoven M, Pinard E, Roche O, Rogers-Evans M. WO2009016087A1, 2009
    • 1f Crowley CA, Delaet NG. J, Ernst J, Grove CG, Hepburn B, King B, Larson CJ, Miller S, Pryor K, Shuster LJ. WO2007146712A2, 2007
    • 2a Chu W, Zhang J, Zeng C, Rothfuss J, Tu Z, Chu Y, Reichert DE, Welch MJ, Mach RH. J. Med. Chem. 2005; 48: 7637
    • 2b Lin Y.-F, Lai T.-C, Chang C.-K, Chen C.-L, Huang M.-S, Yang C.-J, Liu H.-G, Dong J.-J, Chou Y.-A, Teng K.-H, Chen S.-H, Tian W.-T, Jan Y.-H, Hsiao M, Liang P.-H. J. Clin. Invest. 2013; 123: 3861
    • 2c Hagihara M, Schreiber SL. J. Am. Chem. Soc. 1992; 14: 6570
    • 2d Dubowchik GM, Ditta JL, Herbst JJ, Bollini S, Vinitsky A. Bioorg. Med. Chem. Lett. 2000; 10: 559
    • 3a Wang XJ, Etzkorn FA. Biopolymers 2006; 84: 125
    • 3b Curtin M, Glaser K. Curr. Med. Chem. 2003; 10: 2373
    • 3c Coffinier D, El Kaim L, Grimaud L. Org. Lett. 2009; 11: 1825
    • 3d Zhang Z, Zhang Q, Ni Z, Liu Q. Chem. Commun. 2010; 46: 1269
    • 3e Natarajan A, Wang K, Ramamurthy V, Scheffer JR, Patrick B. Org. Lett. 2002; 4: 1443
    • 3f Sai KK. S, Esteves PM, Tanoue da Penha E, Klumpp DA. J. Org. Chem. 2008; 73: 6506
    • 3g Tomita D, Yamatsugu K, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2009; 131: 6946
    • 4a Hua R, Takeda H, Abe Y, Tanaka M. J. Org. Chem. 2004; 69: 974
    • 4b Mossetti R, Pirali T, Tron GC, Zhu J. Org. Lett. 2010; 12: 820
    • 4c Chen J, Cunico RF. J. Org. Chem. 2004; 69: 5509
    • 4d Singh RP, Shreeve JN. M. J. Org. Chem. 2003; 68: 6063
    • 5a Zhang C, Jiao N. J. Am. Chem. Soc. 2010; 132: 28
    • 5b Xu C.-F, Xu M, Jia Y.-X, Li C.-Y. Org. Lett. 2011; 13: 1556
    • 5c Deshidi R, Kumar M, Devari S, Shah BA. Chem. Commun. 2014; 50: 9533
    • 6a Al-Rashid ZF, Johnson WL, Hsung RP, Wei Y, Yao P.-Y, Liu R, Zhao K. J. Org. Chem. 2008; 73: 8780
    • 6b Zhang C, Xu Z, Zhang L, Jiao N. Angew. Chem. Int. Ed. 2011; 50: 11088
    • 7a Uozumi Y, Arii T, Watanabe T. J. Org. Chem. 2001; 66: 5272
    • 7b Liu J, Zhang R, Wang S, Sun W, Xia C. Org. Lett. 2009; 11: 1321
    • 7c de la Fuente V, Godard C, Zangrando E, Claver C, Castillon S. Chem. Commun. 2012; 48: 1695
    • 7d Tsukada N, Ohba Y, Inoue Y. J. Organomet. Chem. 2003; 687: 436
    • 7e Ozawa F, Soyama H, Yanagihara H, Aoyama I, Takino H, Izawa K, Yamamoto T, Yamamoto A. J. Am. Chem. Soc. 1985; 107: 3235
    • 7f Wang Y, Yang X, Zhang C, Yu J, Liu J, Xia C. Adv. Synth. Catal. 2014; 356: 2539
    • 8a Grassot J.-M, Masson G, Zhu J. Angew. Chem. Int. Ed. 2008; 47: 947
    • 8b Bouma M, Masson G, Zhu J. J. Org. Chem. 2010; 75: 2748
    • 8c Giustiniano M, Mercalli V, Cassese H, Di Maro S, Galli U, Novellino E, Tron GC. J. Org. Chem. 2014; 79: 6006
    • 9a Zhang X, Yang W, Wang L. Org. Biomol. Chem. 2013; 11: 3649
    • 9b Li D, Wang M, Liu J, Zhao Q, Wang L. Chem. Commun. 2013; 49: 3640
    • 9c Wang H, Guo L.-N, Duan X.-H. Org. Biomol. Chem. 2013; 11: 4573
    • 10a Song B, Wang S, Sun C, Deng H, Xu B. Tetrahedron Lett. 2007; 48: 8982
    • 10b Du B, Jin B, Sun P. Org. Biomol. Chem. 2014; 12: 4586
    • 10c Song B, Wang S, Sun C, Deng H, Xu B. Tetrahedron Lett. 2007; 48: 8982
    • 11a Zhang C, Zong X, Zhang L, Jiao N. Org. Lett. 2012; 14: 3280
    • 11b Shaw AY, Denning CR, Hulme C. Tetrahedron Lett. 2012; 53: 4151
    • 11c Mupparapu N, Khan S, Battula S, Kushwaha M, Gupta AP, Ahmed QN, Vishwakarma RA. Org. Lett. 2014; 16: 1152
    • 12a Du F.-T, Ji J.-X. Chem. Sci. 2012; 3: 460
    • 12b Lamani M, Prabhu KR. Chem. Eur. J. 2012; 18: 14638
    • 12c Zhao Q, Miao T, Zhang X, Zhou W, Wang L. Org. Biomol. Chem. 2013; 11: 1867
    • 12d Mai W.-P, Wang H.-H, Li Z.-C, Yuan J.-W, Xiao Y.-M, Yang L.-R, Mao P, Qu L.-B. Chem. Commun. 2012; 48: 10117
    • 12e Zhang X, Wang L. Green Chem. 2012; 14: 2141
    • 12f Zhou M, Song Q. Synthesis 2014; 46: 1853
    • 12g Zhang Z, Su J, Zha Z, Wang Z. Chem. Commun. 2013; 49: 8982
    • 12h Zhang J, Wei Y, Lin S, Liang F, Liu P. Org. Biomol. Chem. 2012; 11: 9237
  • 13 Wei W, Shao Y, Hu H, Zhang F, Zhang C, Xu Y, Wan X. J. Org. Chem. 2012; 77: 7157
    • 14a Mannam S, Sekar G. Synth. Commun. 2010; 40: 2822
    • 14b Mannam S, Alamsetti SK, Sekar G. Adv. Synth. Catal. 2007; 349: 2253
    • 14c Mannam S, Sekar G. Tetrahedron Lett. 2008; 49: 2457
    • 14d Mannam S, Sekar G. Tetrahedron Lett. 2008; 49: 1083
    • 14e Thakur KG, Sekar G. Chem. Commun. 2011; 47: 5076
    • 14f Thakur KG, Sekar G. Chem. Commun. 2011; 47: 6692
    • 14g Jaseer EA, Prasad DJ. C, Dandapathy A, Sekar G. Tetrahedron Lett. 2010; 51: 5009
    • 14h Alamsetti SK, Poonguzhali E, Ganapathy D, Sekar G. Adv. Synth. Catal. 2013; 355: 2803
  • 15 When acyclic amines such as N,N-diethylamine, N,N-diallylamine, N,N-diisopropylamine and N,N-dibenzylamine were used under the same reaction conditions, all gave inseparable complex mixtures (numerous spots by TLC).