Aryl fluoride syntheses involving reaction of aryllead triacetates with boron trifluoride-diethyl ether complex

Abstract

Aryllead(IV) triacetates react at room temperature with BF 3.Et 2O to give the corresponding aryl fluoride in moderate to good yields; triarylboroxines, electron rich aryltrimethylsilanes and some arenes, which yield aryllead triacetates in acid catalysed reactions with lead tetraacetate, are converted directly into aryl fluorides when stirred with lead tetraacetate in BF 3.Et 2O. An investigation of the mechanism of the fluoro-deplumbation reaction indicates that it probably proceeds by acid catalysed heterolytic cleavage of the CPb bond to produce an aryl cation.