(Phenyl)[ o-(Trimethylsilyl)phenyl]iodonium Triflate. A N e w and Efficient Benzyne Precursor of

Abstract

(P h en y I) [ 0-(t r i m et h y I s i I y I) p h e n y I I i o d o n i u m t r if I a t e read i I y p re pa red fro m 0-b i s(t r i m et h y I s i I y I) be n ze n e a n d the hypervalent iodine(iti) reagent [ P ~ I (O A C) ~ . ~ T ~ O H I shows excellent formation of benzyne under mild and neutral conditions and efficiently provides adducts with typical trapping agents, e.g. furan, anthracene, dip hen y I is0 be nzof u ran and tetra p he n y lcyclo pentad ie none. Benzyne 1 is an important reactive intermediate and many studies on its generation and reactions have been undertaken.1 Many methods of generating benzyne from a variety of precursors such as o-halogenophenyl anions 2, benzenediazo-nium-2-carboxylate 3, diphenyliodonium-2-carboxylate 4 and