Synthesis of Silylbiaryl Triflates by Chemoselective Suzuki Reaction

Abstract

A modular approach for the synthesis of functionalized silylbiaryl triflates has been developed. Iodinated silylaryl triflates were prepared via a gram-scale diiodination reaction, followed by a one-flask transformation, in 42–52% overall yield. The iodinated silylaryl triflates were subjected to a novel chemoselective Suzuki reaction with arylboronic acids, using PdCl₂(PPh₃)₂ as catalyst and K₂CO₃ as base in THF/H₂O (1:1) at 80 °C for 24 hours, which afforded silylbiaryl triflates in 47–81% yield.

Key words

iodinated silylaryl triflates - chemoselective cross-coupling - Suzuki reaction - silylbiaryl triflates - benzyne chemistry

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