The lecture conveys a personal account on research carried out during two decades involving fluorine in several roles. The serendipitous discovery of the beneficial effect of fluoride salts in two transition-metal-catalyzed enantioselective reactions [1,2] instigated the work towards the first enantioselective catalytic fluorination [3]. The latter, in turn, could only be realized via an instructive failure [4] and a change in concept, from a nucleophilic to an electrophilic fluorination approach. Some mechanistic understanding of the Ti-catalyzed fluorination 1,3-dicarbonyl compounds with e.g. Selectfluor [5] combined with the naive thinking that the trifluoromethyl group is a pseudo halogen finally led to the design of hypervalent iodine reagents for perfluoroalkylation [6]. Newest developments in this area will be touched upon.<br/>

<b>Award Address</b> (ACS Award for Creative Work in Fluorine Chemistry sponsored by the ACS Division of Fluorine Chemistry). Contributing to organofluorine chemistry as an outsider

253rd National Meeting (2017)

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Award Address (ACS Award for Creative Work in Fluorine Chemistry sponsored by the ACS Division of Fluorine Chemistry). Contributing to organofluorine chemistry as an outsider