A facile synthesis of sulfonate esters from phenols using catalytic KF/NFSI and K2CO3

An effective approach toward conversion of phenols to their benzene sulfonate esters by using N-fluorobenzenesufonimide (NFSI) and catalytic potassium fluoride is demonstrated. Mild reaction conditions, shorter reaction time, excellent yield and easy-to-handle reagents are the key features of the me...

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Bibliographic Details
Published inChemical papers Vol. 77; no. 3; pp. 1765 - 1772
Main Authors Dond, Bharat D., Pansare, Dattatraya N., Sarkate, Aniket P., Thore, Shivaji N.
Format Journal Article
LanguageEnglish
Published Warsaw Versita 01.03.2023
Springer Nature B.V
Subjects
Benzene
Biochemistry
Biotechnology
Catalytic converters
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Esters
Industrial Chemistry/Chemical Engineering
Materials Science
Medicinal Chemistry
Phenols
Potassium carbonate
Potassium fluoride
Reaction time
Reagents
Short Communication
Substrates
Phenols
Benzene sulfonate esters
NFSI
Potassium fluoride
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Summary:An effective approach toward conversion of phenols to their benzene sulfonate esters by using N-fluorobenzenesufonimide (NFSI) and catalytic potassium fluoride is demonstrated. Mild reaction conditions, shorter reaction time, excellent yield and easy-to-handle reagents are the key features of the methodology. Mild reaction conditions have conferred wide substrate tolerability and sensitive substrates are well preserved during the reaction. Sulfonate ester formation is governed by benzenesulfonyl fluoride which is in situ generated after addition of KF to NFSI and KF is regenerated after sulfonylation when potassium carbonate is used as a base. Graphical Abstract
ISSN:0366-6352
1336-9075
2585-7290
DOI:10.1007/s11696-022-02585-3