Diphenylammonium triflate (DPAT): Efficient catalyst for esterification of carboxylic acids and for transesterification of carboxylic esters with nearly equimolar amounts of alcohols

Tetrahedron Letters

Volumn 41, Issue 27, 2000, Pages 5249-5252

  Wakasugi, Kazunori ^a   Misaki, Tomonori ^a   Yamada, Kayo ^a   Tanabe, Yoo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; ESTERIFICATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034234818     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00821-2     Document Type: Article

References (15)

1. (a) Beaz, G. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, p. 323.
2. (b) Otera, J. Chem. Rev. 1993, 93, 1449.
3. (c) Franklin, A. S. J. Chem. Soc., Perkin Trans. 1 1998, 2451 and 1999, 3537.
4. Otera, J.; Dan-oh, N.; Nozaki, H. J. Org. Chem. 1991, 56, 5307.
5. (a) Shiina, I.; Mukaiyama, T.; Miyoshi, S.; Miyashita, M. Chem. Lett. 1994, 515.
6. (b) Mukaiyama, T.; Shiina, I. Chem. Lett. 1995, 141.
7. 2NH (0.85 g, 5.0 mmol) in toluene (10.0 ml) at 20-25°C, and the mixture was stirred for 15 min. Evaporation of the solvent gave the crude product, which was washed with hexane (ca. 50 ml) to give a pure DPAT (1.55 g, 97%) as colorless crystals (mp 172-173°C).
8. Miyashita, M.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772.
9. - did not crystallize, so they were excluded from this investigation.
10. 3CN (46%), DME (27%), DMF (trace).
11. Typical procedure: 3-Phenylpropionic acid (150 mg, 1.0 mmol), 1-octanol (130 mg, 1.0 mmol), and DPAT (3.2 mg, 0.01 mmol) were heated (80°C) in toluene for 4 h. Evaporation of toluene (ca. 40°C) under reduced pressure gave the crude material, which was purified by column chromatography (hexane:ether=10:1) to give the desired carboxylic ester (244 mg, 93%). For recent representative works, see: (a) Masaki, Y.; Tanaka, N.; Miura, T. Chem. Lett. 1997, 55.
12. (b) Ponde, D. E.; Deshpande, V. H.; Bulbule, V. J.; Sudalai, A.; Gajare, A. S. J. Org. Chem. 1998, 63, 1058.
13. (c) Furlan, R. L. E.; Mata, E. G.; Mascaretti, O. A. Tetrahedron Lett. 1998, 39, 2257.
14. (d) Krasik, P. Tetrahedron Lett. 1998, 39, 4223.
15. 2 the transesterification is smoother than the esterification. In contrast, the present method shows a reverse relationship.