Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.tet.2012.08.024
Title: Dimethylbut-2-ynedioate mediated esterification of acids via sp 3 C-N bond cleavage of benzylic tertiary amines
Authors: Shen, H.
Lu, X.
Jiang, K.-Z.
Yang, K.-F.
Lu, Y. 
Zheng, Z.-J.
Lai, G.-Q.
Xu, L.-W.
Keywords: Acid
C-N cleavage
Esterification
Silanes
Tertiary amine
Issue Date: 28-Oct-2012
Citation: Shen, H., Lu, X., Jiang, K.-Z., Yang, K.-F., Lu, Y., Zheng, Z.-J., Lai, G.-Q., Xu, L.-W. (2012-10-28). Dimethylbut-2-ynedioate mediated esterification of acids via sp 3 C-N bond cleavage of benzylic tertiary amines. Tetrahedron 68 (43) : 8916-8923. ScholarBank@NUS Repository. https://doi.org/10.1016/j.tet.2012.08.024
Abstract: A straightforward synthetic transformation of tertiary amines to the esterification of equimolar amounts of acids was demonstrated in this manuscript. The present protocol can be regarded as a straightforward synthetic transformation of tertiary amines to the esterification of equimolar amounts of acid. Moreover, the reaction is fundamentally new chemistry for the sp 3 C-N bond cleavage coupled with esterification. The esterification reaction conditions are very mild and functional group-tolerated, such as hydrosilanes, alcohols, phenol, and amino acids. A mechanism is proposed in which the tertiary amine reacts with dimethyl but-2-ynedioate to form zwitterionic salt, and then the zwitterionic intermediate subsequently accept hydrogen to assist the nucleophilic attack of oxygen atom of carboxyl group at the benzyl group of tertiary amine, while a separate reaction pathway leads to esterification. © 2012 Elsevier B.V. All rights reserved.
Source Title: Tetrahedron
URI: http://scholarbank.nus.edu.sg/handle/10635/93590
ISSN: 00404020
DOI: 10.1016/j.tet.2012.08.024
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