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

Connor P. Delaney, Vincent M. Kassel, Scott E. Denmark

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)73-80
Number of pages8
JournalACS Catalysis
DOIs
StateAccepted/In press - Jan 1 2019

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Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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