Potassium Trimethylsilanolate Enables Rapid, Homogeneous Suzuki-Miyaura Cross-Coupling of Boronic Esters

ACS Catal. 2020 Jan 3;10(1):73-80. doi: 10.1021/acscatal.9b04353. Epub 2019 Dec 2.

Abstract

Herein, a mild and operationally simple method for the Suzuki-Miyaura cross-coupling of boronic esters is described. Central to this advance is the use of the organic-soluble base, potassium trimethylsilanolate, which allows for a homogeneous, anhydrous cross-coupling. The coupling proceeds at a rapid rate, often furnishing products in quantitative yield in less than 5 min. By applying this method, a >10-fold decrease in reaction time was observed for three published reactions which required >48 h to reach satisfactory conversion.

Keywords: Suzuki–Miyaura reaction; cross-coupling; homogeneous catalysis; palladium; synthetic methods.