Synthesis of a new hypervalent iodine compound, [2-(hydroxydimethylsilyl)phenyl](phenyl)iodonium triflate as a convenient approach to benzyne

Abstract

A new benzyne precursor, [2-(hydroxydimethylsilyl)phenyl](phenyl)iodonium triflate, is prepared from 1,2-dibromobenzene in good yield. This procedure avoids the use of carcinogenic HMPA and the severe reaction conditions. The reaction of the benzyne precursor with Bu 4NF in the presence of a trapping agent under very mild conditions efficiently generates benzyne and gives the benzyne adduct in high yield.