Development of fluorous Lewis acid-catalyzed reactions

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 implemen...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2006-08, Vol.11 (8), p.627-640
Main Authors: Yoshida, Akihiro, Hao, Xiuhua, Yamazaki, Osamu, Nishikido, Joji
Format: Article
Language:English
Subjects:
Acids - chemistry
aqueous reaction
biphasic system
Carbon Dioxide - chemistry
Catalysis
Fluorocarbons - chemistry
Fluorous chemistry
Green chemistry
Lewis acid
Organometallic Compounds - chemistry
Review
Silica Gel
Silicon Dioxide - chemistry
Sulfonamides - chemistry
sulfonimide
Water - chemistry
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/11080627