DPAT (1) is a useful esterification catalyst developed by Tanabe et al. affording esters in high yields from equimolar amounts of carboxylic acids and alcohols under mild reaction condition.1a-c) In this case, desired esters can be obtained by simple operation without addition of dehydrating agent and azeotropic water removal. There is also a report using fluorous solvent, in which 1 is useful for the substrate with high steric hindrance.1d)
PFPAT (2) shows higher activity than 1 and it can be applied widely to esterification and lactonization.1b,c) Furthermore, 2 can be removed after work-up; washing with NaOH aqueous solution removed CF3SO3H, followed by distillation (C6F5NH2: bp 153℃ / 760 mmHg). 2 is expected to be applied to various fields because it has high activity and it can be removed easily after the reaction.
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Useful Ammonium Triflate Catalysts for Esterification
No.138(August 2009)
References
- 1)Effective methods for the catalytic esterification using ammonium triflate catalyst
- a)K. Wakasugi, T. Misaki, K. Yamada, Y. Tanabe, Tetrahedron Lett. 2000, 41, 5249.
- b)Y. Tanabe, T. Misaki, A. Iida, Y. Nishii, Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Japan) 2004, 62, 1249.
- c)T. Funatomi, K. Wakasugi, T. Misaki, Y. Tanabe, Green Chemistry 2006, 8, 1022.
- d)B. Gacem, G. Jenner, Tetrahedron Lett. 2003, 44, 1391.
- 2)Other applications
- a)Selective N,N-dimethylation of primary aromatic amines with dimethyl carbonate Z. L. Shen, X. Z. Jiang, J. Mol. Catal. A: Chem. 2004, 213, 193.
- b)C-Acylation of enol silyl ethers or ketene silyl (thio)acetals with acid chlorides A. Iida, J. Osada, R. Nagase, T. Misaki, Y. Tanabe, Org. Lett. 2007, 9, 1859.
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