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

Nidhi Sharma; Surya Srinivas Kotha; Nabajit Lahiri; Govindasamy Sekar

doi:10.1055/s-0034-1379975

Synthesis, Table of Contents

Synthesis 2015; 47(05): 726-736
DOI: 10.1055/s-0034-1379975

paper

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

› Author Affiliations

Abstract

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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.

Key words

copper catalyst - one-pot synthesis - oxidative amidation - α-ketoamides - 1-arylethanols

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References

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).

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