The use of catalysts in the activation of carboxyl groups towards nucleophilic attack and the protection of other functional groups by suitable protecting groups are standard and necessary procedures in amide bond formation. In contrast to the usual methods, various new compounds, amides of APTES ((3-aminopropyl)triethoxysilane, 3-triethoxysilylpropylamine) and carboxyphenylboronic acids, as well as the amides of aniline and carboxyphenylboronic acids, were obtained in good yields by a one-step synthesis under mild conditions without using any coupling reagents or additional catalysts.
References
Al-Zoubi, R. M., Marion, O., & Hall, D. G. (2008). Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature. Angewandte Chemie International Edition, 47, 2876–2879. DOI: 10.1002/anie.200705468.10.1002/anie.200705468Search in Google Scholar PubMed
Anderson, G. W., Zimmerman, J. E., & Callahan, F. M. (1964). The use of esters of N-hydroxysuccinimide in peptide synthesis. Journal of the American Chemical Society, 86, 1839–1842. DOI: 10.1021/ja01063a037.10.1021/ja01063a037Search in Google Scholar
Gu, L., Lim, J., Cheong, J. L., & Lee, S. S. (2014). MCF-supported boronic acids as efficient catalysts for direct amide condensation of carboxylic acids and amines. Chemical Communications, 50, 7017–7019. DOI: 10.1039/c4cc01148a.10.1039/c4cc01148aSearch in Google Scholar PubMed
Jursic, B. S., & Zdravkovski, Z. (1993). A simple preparation of amides from acids by heating of their mixture. Synthetic Communications, 23, 2761–2770. DOI: 10.1080/00397919308013807.10.1080/00397919308013807Search in Google Scholar
Lanigan, R. M., Starkov, P., & Sheppard, T. D. (2013). Direct synthesis of amides from carboxylic acids and amines using B(OCH2CF3)3. The Journal of Organic Chemistry, 78, 4512–4523. DOI: 10.1021/jo400509n.10.1021/jo400509nSearch in Google Scholar PubMed PubMed Central
Lundberg, H., Tinnis, F., Selander, N., & Adolfsson, H. (2014). Catalytic amide formation from non-activated carboxylic acids and amines. Chemical Society Reviews, 43, 2714–2742. DOI: 10.1039/c3cs60345h.10.1039/c3cs60345hSearch in Google Scholar PubMed
Montalbetti, C. A. G. N., & Falque, V. (2005). Amide bond formation and peptide coupling. Tetrahedron, 61, 10827–10852. DOI: 10.1016/j.tet.2005.08.031.10.1016/j.tet.2005.08.031Search in Google Scholar
Mylavarapu, R. K., Kondaiah, G. C. M., Kolla, N., Veeramalla, R., Koilkonda, P., Bhattacharya, A., & Bandichhor, R. (2007). Boric acid catalyzed amidation in the synthesis of active pharmaceutical ingredients. Organic Process Research & Development, 11, 1065–1068. DOI: 10.1021/op700098w.10.1021/op700098wSearch in Google Scholar
Noda, H., & Bode, J. W. (2014). Synthesis and chemoselective ligations of MIDA acyloboronates with O-Me hydroxylamines. Chemical Science, 5, 4328–4332. DOI: 10.1039/c4sc00971a.10.1039/c4sc00971aSearch in Google Scholar
Sheehan, J., Cruickshank, P., & Boshart, G. (1961). A convenient synthesis of water-soluble carbodiimides. The Journal of Organic Chemistry, 26, 2525–2528. DOI: 10.1021/jo01351a600.10.1021/jo01351a600Search in Google Scholar
Tam, E. K. W., Rita, Liu, L. Y., & Chen, A. (2015). 2-Furanylboronic acid as an effective catalyst for the direct amidation of carboxylic acids at room temperature. European Journal of Organic Chemistry, 2015, 1100–1107. DOI: 10.1002/ejoc.201403468.10.1002/ejoc.201403468Search in Google Scholar
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