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

Connor P. Delaney | Zendy; Vincent M. Kassel | Zendy; Scott E. Denmark | Zendy

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Potassium 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.

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