Fluoroalkanes, reduction

Alkyl fluorides are for practical purposes resistant to reduction. In a few instances, where fluorine in fluoroalkanes was replaced by hydrogen, very energetic conditions were required and usually gave poor yields 500, SOI], For this reason it is not difficult to replace other halogens present in the molecule without affecting fluorine. 

Alternatively, several non-halogen electrophiles, for example dimethyl(methyl-thio)sulfonium tetrafluoroborate [64] or N-phenylselenylphthalimide (NPSP) have been used [65], The phenylselenyl moiety can be removed later, either by using m-chloroperbenzoic acid (MCPBA) to give fluoroalkenes or by radical reduction to furnish the fluoroalkane (Scheme 2.23). 

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