Because of the unique properties of fluorine and C-F bond, incorporation of fluorine into organic molecules can often change their chemical, physical, and biological properties. Therefore, a number of applications of organofluorine compounds have been found in medicinals, agrochemicals, functional materials, and other fields [1, 2, 3, 4]. The fluorine effect has been widely used in lipophilicity tuning, pKa modulation, and selective blocking of oxidative metabolism [3, 5]. Due to easy availability of alcohols, many efforts have been devoted to the development of reagents and reactions for converting alcohols to fluorinated compounds [6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17]. As early as the 1960s, several phosphine-based deoxofluorinating reagents were developed. This chapter summarizes synthesis and application of the phosphine-based reagents, difluoro(triphenyl)phosphorane (Ph3PF2), trifluoro(diphenyl)phosphorane (Ph2PF3), and tetrafluoro(phenyl)phosphorane (PhPF4) [18...
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