Open AccessPotassium Trimethylsilanolate Enables Rapid, Homogeneous Suzuki−Miyaura Cross-Coupling of Boronic Esters
Author(s) -
Connor P. Delaney,
Vincent M. Kassel,
Scott E. Denmark
Publication year - 2019
Publication title -
acs catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 4.898
H-Index - 198
ISSN - 2155-5435
DOI - 10.1021/acscatal.9b04353
Subject(s) - anhydrous , yield (engineering) , chemistry , potassium , homogeneous , combinatorial chemistry , coupling reaction , base (topology) , boronic acid , catalysis , coupling (piping) , organic chemistry , materials science , thermodynamics , mathematics , mathematical analysis , physics , metallurgy
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.