Understanding Site Selectivity in the Palladium-Catalyzed Cross-Coupling of Allenylsilanolates

Scott E. Denmark, Andrea Ambrosi

Research output: Contribution to journalArticle

Abstract

Allenylsilanolates can undergo cross-coupling at the α- or γ-terminus, and site selectivity appears to be determined by the intrinsic transmetalation mechanism. Fine-tuning of concentration, nucleophilicity, and steric bulk of the silanolate moiety allows for the selective formation of one isomer over the other. Whereas the α-isomer can be obtained in synthetically useful yield, the γ-isomer is favored only when employing reaction conditions that are inevitably associated with diminished reactivity.

Original languageEnglish (US)
Pages (from-to)2415-2420
Number of pages6
JournalSynlett
Volume28
Issue number18
DOIs
StatePublished - Nov 13 2017

Keywords

  • allenes
  • cross-coupling
  • organosilanes
  • palladium
  • site selectivity
  • transmetalation

ASJC Scopus subject areas

  • Organic Chemistry

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