Palladium-catalyzed cross-coupling reactions of silanolates: A paradigm shift in silicon-based cross-coupling reactions

Scott E Denmark, John D. Baird

Research output: Contribution to journalArticle

Abstract

This paper chronicles the conceptual development, proof of principle experiments, and recent advances in the palladium-catalyzed cross-coupling reactions of the conjugate bases of organosilanois. The discovery that led to the design and refinement of this process represents a classical illustration of how mechanistic studies can provide a fertile ground for the invention of new reactions. On the basis of a working hypothesis (which ultimately proved to be incorrect) and the desire to effect silicon-based cross-coupling without the agency of fluoride activation, a mild and practical palladium-catalyzed cross-coupling of alkenyl-, aryl-, and heteroaryl silanolates has been -developed. The mechanistic underpinnings, methodological extensions, and the successful applications of this technology to the synthesis of complex molecules are described.

Original languageEnglish (US)
Pages (from-to)4954-4963
Number of pages10
JournalChemistry - A European Journal
Volume12
Issue number19
DOIs
StatePublished - Jun 23 2006

Keywords

  • Cross-coupling
  • Green chemistry
  • Organosili-con
  • Palladium
  • Silanolates

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Palladium-catalyzed cross-coupling reactions of silanolates: A paradigm shift in silicon-based cross-coupling reactions'. Together they form a unique fingerprint.

  • Cite this