Jump to main content
Jump to site search

Issue 12, 2006
Previous Article Next Article

Pentafluorophenylammonium triflate (PFPAT): an efficient, practical, and cost-effective catalyst for esterification, thioesterification, transesterification, and macrolactone formation

Author affiliations

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.

Graphical abstract: Pentafluorophenylammonium triflate (PFPAT): an efficient, practical, and cost-effective catalyst for esterification, thioesterification, transesterification, and macrolactone formation

Back to tab navigation

Article information


Submitted
28 Jun 2006
Accepted
18 Aug 2006
First published
07 Sep 2006

Green Chem., 2006,8, 1022-1027
Article type
Paper

Pentafluorophenylammonium triflate (PFPAT): an efficient, practical, and cost-effective catalyst for esterification, thioesterification, transesterification, and macrolactone formation

T. Funatomi, K. Wakasugi, T. Misaki and Y. Tanabe, Green Chem., 2006, 8, 1022
DOI: 10.1039/B609181B

Social activity

Search articles by author

Spotlight

Advertisements