Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Letter Article

Thiourea-Catalyzed Amidation of Esters: A New Method for the Preparation of Amides

Author(s): Audrey B. Garza, Rebecca G. Miller, Steven B. Gardner, Timothy J. Fuhrer, Alicia B. Campbell and Todd A. Davis*

Volume 20, Issue 1, 2023

Published on: 06 June, 2022

Page: [2 - 10] Pages: 9

DOI: 10.2174/1570178619666220615144433

Price: $65

Abstract

Although amides are one of the most abundant bonds in biology and medicinal chemistry, methods to prepare them are still limited. To expand on current methods for the formation of amides bonds, organocatalysts (thiourea-based) were developed to mediate the conversion of esters to amides. The reactions proceed in good to moderate yields and tolerate a variety of functional groups. 1H NMR titration and computational studies show a strong hydrogen-bonding interaction between the thiourea catalyst and the ester moiety. This hydrogen-bonding interaction is proposed to be the driving force for the amidation of esters.

Keywords: Organocatalysis, Thiourea, Amide synthesis, 1H NMR titrations, organic synthesis

« Previous Next »
Graphical Abstract

[1]
Greenberg, A.; Breneman, C.M.; Liebman, J.F. Wiley-Interscience: New York, 2000.
[2]
Pattabiraman, V.R.; Bode, J.W. Nature, 2011, 480(7378), 471-479.
[http://dx.doi.org/10.1038/nature10702] [PMID: 22193101]
[3]
de Figueiredo, R.M.; Suppo, J.S.; Campagne, J.M. Chem. Rev., 2016, 116(19), 12029-12122.
[http://dx.doi.org/10.1021/acs.chemrev.6b00237] [PMID: 27673596]
[4]
Miller, S.A.; Leadbeater, N.E. RSC Advances, 2015, 5(113), 93248-93251.
[http://dx.doi.org/10.1039/C5RA21394K]
[5]
Ohshima, T.; Hayashi, Y.; Agura, K.; Fujii, Y.; Yoshiyama, A.; Mashima, K. Chem. Commun. (Camb.), 2012, 48(44), 5434.
[http://dx.doi.org/10.1039/c2cc32153j]
[6]
Morimoto, H.; Fujiwara, R.; Shimizu, Y.; Morisaki, K.; Ohshima, T. Org. Lett., 2014, 16(7), 2018-2021.
[http://dx.doi.org/10.1021/ol500593v] [PMID: 24660939]
[7]
(a) Singh, C.; Kumar, V.; Sharma, U.; Kumar, N.; Singh, B. Lett. Org. Chem., 2013, 10, 241-264.;
(b) Hie, L.; Fine Nathel, N.F.; Hong, X.; Yang, Y-F.; Houk, K.N.; Garg, N.K. Angew. Chem. Int. Ed., 2016, 55, 2810-2814.
[http://dx.doi.org/10.1002/anie.201511486];
(c) Whittaker, A.M.; Dong, V.M. Angew. Chem. Int. Ed., 2015, 54(4), 1312-1315.
[http://dx.doi.org/10.1002/anie.201410322];
(d) Ling, L.; Chen, C.; Luo, M.; Zeng, X. Org. Lett., 2019, 21(6), 1912-1916.
[http://dx.doi.org/10.1021/acs.orglett.9b00554] [PMID: 30835488];
(e) Han, Q.; Xiong, X.; Li, S. Catal. Commun., 2015, 58, 85-88.
[http://dx.doi.org/10.1016/j.catcom.2014.08.036];
(f) Halima, T.B.; Vandavasi, J.K.; Shkoor, M.; Newman, S.G. ACS Catal., 2017, 7, 2176-2180.
[http://dx.doi.org/10.1021/acscatal.7b00245]
[8]
Doyle, A.G.; Jacobsen, E.N. Chem. Rev., 2007, 107(12), 5713-5743.
[http://dx.doi.org/10.1021/cr068373r] [PMID: 18072808]
[9]
Nagorny, P.; Sun, Z. Beilstein J. Org. Chem., 2016, 12, 2834-2848.
[http://dx.doi.org/10.3762/bjoc.12.283] [PMID: 28144357]
[10]
(a) Zuend, S.J.; Jacobsen, E.N. J. Am. Chem. Soc., 2007, 129(51), 15872-15883.
[http://dx.doi.org/10.1021/ja0735352] [PMID: 18052247];
(b) Vachal, P.; Jacobsen, E.N. J. Am. Chem. Soc., 2002, 124(34), 10012-10014.
[http://dx.doi.org/10.1021/ja027246j] [PMID: 12188665];
(c) Kan, W.; Liu, Y.; Deng, Q. Lett. Org. Chem., 2014, 11(10), 755-758.
[http://dx.doi.org/10.2174/157017861110141117145647];
(d) Han, B.; Li, J-L.; Xiao, Y-C.; Zhou, S-L.; Chen, Y-C. Lett. Org. Chem., 2011, 15, 4128-4155.
[11]
(a) Weil, T.; Kotke, M.; Kleiner, C.M.; Schreiner, P.R. Org. Lett., 2008, 10(8), 1513-1516.
[http://dx.doi.org/10.1021/ol800149y] [PMID: 18366220];
(b) Wu, G.; Li, T.; Liu, F.; Zhao, Y.; Ma, S.; Tang, S.; Xie, X.; She, X. Tett Lett., 2021, 81, 153315.
[http://dx.doi.org/10.1016/j.tetlet.2021.153315]
[12]
(a) Menche, D.; Hassfeld, J.; Li, J.; Menche, G.; Ritter, A.; Rudolph, S. Org. Lett., 2006, 8(4), 741-744.
[http://dx.doi.org/10.1021/ol053001a] [PMID: 16468756];
(b) Schreiner, P.; Zhang, Z. Synlett, 2007, 2007(9), 1455-1457.
[http://dx.doi.org/10.1055/s-2007-980349]
[13]
Du, Y.; Li, J.; Chen, K.; Wu, C.; Zhou, Y.; Liu, H. Beilstein J. Org. Chem., 2017, 13, 1342-1349.
[http://dx.doi.org/10.3762/bjoc.13.131] [PMID: 28781700]
[14]
Malamakal, R.M.; Hess, W.R.; Davis, T.A. Org. Lett., 2010, 12(10), 2186-2189.
[http://dx.doi.org/10.1021/ol100647b] [PMID: 20408600]
[15]
Lippert, K.M.; Hof, K.; Gerbig, D.; Ley, D.; Hausmann, H.; Guenther, S.; Schreiner, P.R. Eur. J. Org. Chem., 2012, 2012(30), 5919-5927.
[http://dx.doi.org/10.1002/ejoc.201200739]
[16]
Carey, F.A.; Sundberg, R.J. Springer: New York, 2007.
[17]
Nguyen, T.B.; Ermolenko, L.; Al-Mourabit, A. Green Chem., 2013, 15(10), 2713.
[http://dx.doi.org/10.1039/c3gc41186a]
[18]
Liu, L.; Zhang, S.; Fu, X.; Yan, C.H. Chem. Commun. (Camb.), 2011, 47(36), 10148.
[http://dx.doi.org/10.1039/c1cc13202d]
[19]
Kobayashi, K.; Asakawa, Y.; Kikuchi, Y.; Toi, H. J. Am. Chem. Soc., 1993, 115, 2648-2654.
[http://dx.doi.org/10.1021/ja00060a013]
[20]
Luchini, G.; Ascough, D.M.H.; Alegre-Requena, J.V.; Gouverneur, V.; Paton, R.S. Tetrahedron, 2019, 75, 697-702.
[http://dx.doi.org/10.1016/j.tet.2018.12.033]

Rights & Permissions Print Cite
Article Metrics
3
© 2024 Bentham Science Publishers | Privacy Policy