Catalytic application of fluorous silica gel in Fries rearrangement

•Unmodified fluorous silica gel (FSG) was discovered as an efficient catalyst in Fries rearrangement.•A reusable fluorous catalyst system with the advantages of being commercially available was employed.•Ease of work-up, high recovery, low cost of procedure, and simplicity were the other advantages....

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Bibliographic Details
Published in:Journal of fluorine chemistry 2014-04, Vol.160, p.77-81
Main Authors: Ghaffarzadeh, Mohammad, Ahmadi, Maryam
Format: Article
Language:English
Subjects:
Aryl esters
Byproducts
Catalysts
Esters
Fluorous silica gel (Fluoro Flash™)
Fries rearrangement
Recyclability
Silica gel
Solvents
Toxicity
Wastes
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Summary:•Unmodified fluorous silica gel (FSG) was discovered as an efficient catalyst in Fries rearrangement.•A reusable fluorous catalyst system with the advantages of being commercially available was employed.•Ease of work-up, high recovery, low cost of procedure, and simplicity were the other advantages. Commercially available fluorous silica gel (Fluoro Flash™) with no further post-modification was successfully investigated and applied merely as a catalyst in Fries rearrangement of various aryl esters under solvent free conditions in 4h and optimized temperatures. In addition to good yields and recyclability of the catalyst, toxicity of reaction medium, by-products, and wastes were minimized. Also, low catalyst loading was another advantage of this methodology.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2014.01.005