Cross-coupling reactions of alkenylsilanols with fluoroalkylsulfonates: Development and optimization of a mild and stereospecific coupling process

Scott E. Denmark, Christopher S. Regens

Research output: Contribution to journalArticlepeer-review

Abstract

The development of an effective protocol for the palladium-catalyzed cross-coupling of (E)-alkenylsilanols with aryl triflates is described. A critical component in the optimization of this method was balancing the stability and reactivity of the triflates in the presence of a nucleophilic promoter. This report highlights the use of a slightly soluble Brønsted base promoter that allows for a low, steady-state concentration of alkenyl(dimethyl)silanolate in solution, thus facilitating cross-coupling in preference to S-O bond cleavage of the triflate.

Original languageEnglish (US)
Pages (from-to)2165-2168
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number17
DOIs
StatePublished - Apr 27 2011

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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