4.8 Article

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

Journal

ACS CATALYSIS
Volume 10, Issue 1, Pages 73-80

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b04353

Keywords

cross-coupling; Suzuki-Miyaura reaction; homogeneous catalysis; synthetic methods; palladium

Funding

  1. National Institutes of Health [GM R35 127010]

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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.

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