Abstract
Organic synthetic methodology in the 21st century aims to conform to the principles of green sustainable chemistry (GSC) and we may expect that in the future, the realization of GSC will be an important objective for chemical industries. An important aim of synthetic organic chemistry is to implement waste-free and environmentally-benign industrial processes using Lewis acids as versatile as aluminum chloride. A key technological objective of our work in this area has been to achieve a "catalyst recycling system that utilizes the high activity and structural features of fluorous Lewis acid catalysts". Thus, we have developed a series of novel fluorous Lewis acid catalysts, namely the ytterbium(III), scandium(III), tin(IV) or hafnium(IV) bis(perfluoroalkanesulfonyl)amides or tris(perfluoro- alkanesulfonyl)methides. Our catalysts are recyclable and effective for acylations of alcohols and aromatics, Baeyer-Villiger reactions, direct esterifications and transesterifications in a fluorous biphasic system (FBS), in supercritical carbon dioxide and on fluorous silica gel supports.
Highlights
We examined various reactions under fluorous biphasic catalysis, heterogeneous reactions catalyzed by fluorous silica gel-supported fluorous Lewis acid catalysts and fluorous Lewis acid-catalyzed reactions in supercritical carbon dioxide
Socalled “fluorous chemistry” [1] has been studied since 1994, when Horváth and Rábai first reported fluorous biphasic catalysis [2]. Discussions on this topic occurred at the 1st International Symposium on Fluorous Technologies (ISoFT), held in Bordeaux (France) in July 2005, which was attended by chemists from 15 countries and highlighted by Chemical & Engineering News [3]
We review a series of fluorous biphasic reactions catalyzed by fluorous Lewis acids containing a large number of fluorine atoms, heterogeneous Lewis acid-catalyzed reactions using fluorous silica gel-supported fluorous Lewis acids and fluorous Lewis acid-catalyzed reactions in supercritical carbon dioxide
Summary
We examined various reactions under fluorous biphasic catalysis, heterogeneous reactions catalyzed by fluorous silica gel-supported fluorous Lewis acid catalysts and fluorous Lewis acid-catalyzed reactions in supercritical carbon dioxide. A The catalyst in the lower phase was recycled; b Calculated by GC analysis using n-nonane as an internal standard; c Values in parentheses refer to the isolated yields. Our fluorous Lewis acid catalysts, which catalyze several reactions at the organic/fluorous interface, are stable to water due to their highly water-repellent properties.
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