Reactions of Sulfur-and Phosphorus-Substituted Fluoroalkylating Silicon Reagents with Imines and Enamines under Acidic Conditions

MD Kosobokov, AD Dilman, MI Struchkova…

Index: Kosobokov, Mikhail D.; Dilman, Alexander D.; Struchkova, Marina I.; Belyakov, Pavel A.; Hu, Jinbo Journal of Organic Chemistry, 2012 , vol. 77, # 4 p. 2080 - 2086

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Citation Number: 27

Abstract

Nucleophilic fluoroalkylation reactions of imines and enamines with α-phenylthio, α- phenylsulfonyl, and α-diethylphosphoryl substituted fluorinated silanes have been investigated. The reactions are promoted by hydrofluoric acid generated in situ from potassium hydrodifluoride and trifluoroacetic acid. Sulfur reagents worked well with both imines and enamines, whereas phosphorus reagent efficiently coupled only with ...