Pentafluorophenylammonium triflate (PFPAT): an efficient, practical, and cost-effective catalyst for esterification, thioesterification, transesterification, and macrolactone formation
- 7 September 2006
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Green Chemistry
- Vol. 8 (12), 1022-1027
- https://doi.org/10.1039/b609181b
Abstract
A pentafluorophenylammonium triflate (PFPAT) catalyst (1–10 mol%) efficiently promoted esterification and thioesterification between a 1 : 1 mixture of carboxylic acids and alcohols or thiols in good to excellent yield under mild reaction conditions. Transesterification of carboxylic esters with a slight excess of alcohols (1.5 equiv.) also proceeded using the PFPAT catalyst. The PFPAT-catalyzed 13 to 17 membered macrolactone formation of ω-hydroxycarboxylic acids was successfully performed using 10 mol% of the catalyst (total 44 examples). These catalytic condensations have advantages from the viewpoint of green chemistry. PFPAT organocatalyst is air-stable, cost-effective, easy to handle, and easily removed from the reaction mixtures. The operation is quite simple, because a dehydrating system such as the Dean–Stark apparatus is not necessary.This publication has 22 references indexed in Scilit:
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