An Efficient Procedure for the Synthesis of ortho-Trialkylsilylaryl Triflates: Easy Access to Precursors of Functionalized Arynes

Abstract

o-Trialkylsilylaryl triflates, which are useful aryne precursors, are prepared from o-bromophenols by an efficient, one-pot procedure involving O-silylation, metal-halogen exchange, O- to C-silyl migration, and entrapment of the phenoxide with triflic anhydride.

Key words

silylation - triflates - arynes - metalations

References

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  Obtained by the reaction of 2-bromoresorcinol with K₂CO₃ and pent-3-ynyl p-toluenesulfonate.

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Now commercially available from Sigma-Aldrich.