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Dialkylaminodifluorosulfinium tetrafluoroborate salts: synthesis and applications

corresponding

MARC-OLIVIER TURCOTTE-SAVARD1*, OLIVIER MAHÉ2, JEAN-FRANÇOIS PAQUIN2
*Corresponding author
1. OmegaChem, 480, Rue Perreault, Lévis, QC, G6W 7V6, Canada
2. Université Laval, Département de chimie, Canada Research Chair in Organic and Medicinal Chemistry, CCVC, PROTEO, 1045 avenue de la Médecine, Québec, QC, G1V 0A6, Canada

Abstract

The syntheses of dialkylaminodifluorosulfinium tetrafluoroborate salts are described. These reagents, first used for the deoxyfluorination of alcohols, were also shown to fluorinate aldehydes, ketones, carboxylic acids and glycosyl groups. Alternatively, dialkylaminodifluorosulfinium tetrafluoroborate salts were recently shown to act as activating agents for hydroxyl, carbonyl and carboxyl groups in a variety of transformations leading to non-fluorinated products.


INTRODUCTION

With 30 to 40% of agrochemicals and 20 to 25% of pharmaceutical compounds bearing at least one atom of fluorine (1), the development of efficient fluorination methods is a highly active field of research within organic synthesis. Deoxyfluorination represents a valuable strategy to insert fluorine atoms on organic compounds (2). However, deoxyfluorination agents are often hygroscopic, unstable, toxic, hazardous and/or non-selective towards fluorination. Dialkylaminodifluorosulfinium tetrafluoroborate salts (3) were developed as cost effective, safer and more efficient deoxyfluorination reagent when used in conjunction with an appropriate base or fluoride additive (4, 5). Since their first uses, researchers have discovered a number of alternate applic