The fluorocarbon bond has during the past years received increasing attention in modern organic chemistry. It has been widely associated with pharmaceuticals, agrochemicals and pesticides due to the chemical and physical properties of fluorine. The expansion of the C-F bond formation now also calls for selective C-F bond activation. Thus, being able to synthetically alter the robust C-F bond in presence of other functionalities would allow a novel approach in organic synthesis, which enables synthetic diversification of that specific C-F carbon.In a recent publication we describe a novel F/I substitution reaction using YbI3. The substitution was performed in presence of various functional groups, which demonstrates exclusive selectivity for the fluorine atom. Having established the concept, the search for incorporation of further nucleophiles continues. The presentation will cover recent results from the Hilmersson group involving lanthanide(III) promoted F/N substitution. Substrate scope and mechanistic insight will be discussed.

Lanthanide(III) promoted C-F bond substitution: A novel approach for amine incorporation

247th National Meeting (2014)

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