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 degrees C for 24 hours, which afforded silylbiaryl triflates in 47-81% yield.