An Efficient Catalytic Amidation of Esters Promoted by N-Heterocyclic Carbenes

Abstract

An efficient NHC-catalyzed amidation between esters and amines or hydrazines is described. This strategy was tolerant for a wide scope of substrates, affording a series of amides (or hydrazides) in good to excellent yields (60–96%) under simple conditions. The approach was also used to synthesize the pharmaceutically relevant antidepressant moclobemide in 85% yield.

Key words

N-heterocyclic carbenes - amidation - catalytic reaction - amides - nucleophilic addition

• References

• 1 Montalbetti CA. G. N, Falque V. Tetrahedron 2005; 61: 10827
• 2 Pattabiraman VR, Bode JW. Nature 2011; 480: 471
• 3 Allen CL, Williams JM. J. Chem. Soc. Rev. 2011; 40: 3405
• 4 Brown DG, Boström J. J. Med. Chem. 2016; 59: 4443
• 5 Holtmann G, Talley NJ, Liebregts T, Adam B, Parow C. N. Engl. J. Med. 2006; 354: 832
• 6 Lundberg H, Tinnis F, Selander N, Adolfsson H. Chem. Soc. Rev. 2014; 43: 2714
• 7 Carey JS, Laffan D, Thomson C, Williams MT. Org. Biomol. Chem. 2006; 4: 2337

For selected examples, see:
• 8a Maruani A, Lee MT. W, Watkins G, Akhbar AR, Baggs H, Shamsabadi A, Richards DA, Chudasama V. RSC Adv. 2016; 6: 3372
• 8b Pan J, Devarie-Baez NO, Xian M. Org. Lett. 2011; 13: 1092
• 8c Bode JW, Sohn SS. J. Am. Chem. Soc. 2007; 129: 13798
• 8d Guin J, De Sarkar S, Grimme S, Studer A. Angew. Chem. Int. Ed. 2008; 47: 8727
• 8e De Sarkar S, Studer A. Org. Lett. 2010; 12: 1992
• 8f De Sarkar S, Grimme S, Studer A. J. Am. Chem. Soc. 2010; 132: 1190
• 8g Alanthadka A, Maheswari CU. Adv. Synth. Catal. 2015; 357: 1199
• 8h Green RA, Pletcher D, Leach SG, Brown RC. D. Org. Lett. 2016; 18: 1198
• 8i Kumar V, Connon SJ. Chem. Commun. 2017; 53: 10212
• 9 Roy S, Gribble GW. Tetrahedron 2012; 68: 9867

For selected examples, see:
• 10a Yao H, Yamamoto K. Chem. Asian J. 2012; 7: 1542
• 10b Yao H, Tang Y, Yamamoto K. Tetrahedron Lett. 2012; 53: 5094
• 10c Pilo M, Porcheddu A, De Luca L. Org. Biomol. Chem. 2013; 11: 8241
• 10d Dettori G, Gaspa S, Porcheddu A, De Luca L. Adv. Synth. Catal. 2014; 356: 2709
• 10e Tan B, Toda N, Barbas CF. Angew. Chem. Int. Ed. 2012; 51: 12538
• 11 Iqbal N, Cho EJ. J. Org. Chem. 2016; 81: 7453

For selected reviews, see:
• 12a Enders D, Niemeier O, Henseler A. Chem. Rev. 2007; 107: 5606
• 12b Bugaut X, Glorius F. Chem. Soc. Rev. 2012; 41: 3511
• 12c Ryan SJ, Candish L, Lupton DW. Chem. Soc. Rev. 2013; 42: 4906
• 12d Ye S, Chen X.-Y. Synlett 2013; 24: 1614
• 12e Mahatthananchai J, Bode JW. Acc. Chem. Res. 2014; 47: 696
• 12f Flanigan DM, Romanov-Michailidis F, White NA, Rovis T. Chem. Rev. 2015; 115: 9307
• 12g Wang MH, Scheidt KA. Angew. Chem. Int. Ed. 2016; 55: 14912
• 12h Reyes E, Uria U, Carrillo L, Vicario JL. Synthesis 2017; 49: 451
• 12i Kathleen JR, Murauski A, Jaworski A, Scheidt KA. Chem. Soc. Rev. 2018; 47: 1773
• 13 Movassaghi M, Schmidt MA. Org. Lett. 2005; 7: 2453
• 14 Guo H, Wang Y, Du G.-F, Dai B, He L. Tetrahedron 2015; 71: 3472
• 15a Fu Z, Xu J, Zhu T, Leong WW. Y, Chi YR. Nat. Chem. 2013; 5: 835
• 15b Chen S, Hao L, Zhang Y, Tiwari B, Chi YR. Org. Lett. 2013; 15: 5822
• 15c Hao L, Chen S, Xu J, Tiwari B, Fu Z, Li T, Lim J, Chi YR. Org. Lett. 2013; 15: 4956
• 16 Thale PB, Borase PN, Shankarling GS. RSC Adv. 2016; 6: 52724
• 17 Cheng G, Lv W, Kuai C, Wen S, Xiao S. Chem. Commun. 2018; 54: 1726
• 18 Xu X, Feng H, Huang L, Liu X. J. Org. Chem. 2018; 83: 7962
• 19 Wells MJ. M, Clark CR. Anal. Chem. 1992; 64: 1660
• 20 Li F, Wang Z.-M, Wu J.-J, Wang J, Xie S.-S, Lan J.-S, Xu W, Kong L.-Y, Wang X.-B. J. Enzyme Inhib. Med. Chem. 2016; 31: 41
• 21 Tirapegui C, Acevedo-Fuentes W, Dahech P, Torrent C, Barrias P, Rojas-Poblete M, Mascayano C. Bioorg. Med. Chem. Lett. 2017; 27: 1649
• 22 Straub O. Patent US 3073819, 1963
• 23 Ding W, Song Q. Org. Chem. Front. 2015; 2: 765
• 24 Liu P, Tang J, Zeng X. Org. Lett. 2016; 18: 5536
• 25 Zhichkin P, Kesicki E, Treiberg J, Bourdon L, Ronsheim M, Ooi HC, White S, Judkins A, Fairfax D. Org. Lett. 2007; 9: 1415
• 26 Bouma M, Masson G, Zhu J. J. Org. Chem. 2010; 75: 2748
• 27 Maki T, Ishihara K, Yamamoto H. Org. Lett. 2006; 8: 1431