Palladium-catalyzed cross-coupling reactions of substituted aryl(dimethyl)silanols

Scott E Denmark, Michael H. Ober

Research output: Contribution to journalArticle

Abstract

Cesium carbonate and cesium hydroxide monohydrate are effective activators for the palladium-catalyzed cross-coupling of aryl(dimethyl)silanols with substituted aryl halides. Extensive optimization studies led to the identification of key variables (solvent, catalyst, additive, and hydration level) that influence the rate and selectivity of the process. Manipulation of these factors provides an effective coupling method of wide scope and generality. Electron-rich aryl(dimethyl)silanols undergo cross-coupling with aryl iodides and aryl bromides in high yields and high selectivity for the desired cross-coupling products. Alternatively, high yields of cross-coupling products could be obtained with electron-poor or ortho-substituted aryl(dimethyl)silanols when activated with cesium hydroxide monohydrate.

Original languageEnglish (US)
Pages (from-to)1703-1714
Number of pages12
JournalAdvanced Synthesis and Catalysis
Volume346
Issue number13-15
DOIs
StatePublished - Dec 1 2004

Keywords

  • Biaryls
  • C-C bond formation
  • Cesium carbonate
  • Cesium hydroxide
  • Fluoride-free, hydration effect

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Palladium-catalyzed cross-coupling reactions of substituted aryl(dimethyl)silanols'. Together they form a unique fingerprint.

  • Cite this