2-(Chlorodiisopropylsilyl)-6-(trimethylsilyl)phenyl triflate: a modified platform for intramolecular benzyne cycloadditions

Abstract

2-(Chlorodiisopropylsilyl)-6-(trimethylsilyl)phenyl triflate serves as an efficient aryne precursor for intramolecular benzyne [4 + 2] or (2 + 2 + 2) cycloadditions. Key features of this precursor are (1) rapid connection of various arynophiles to the precursor via a Si–O bond and (2) generation of aryne under mild conditions using a combination of Cs₂CO₃ and 18-crown-6.