γ-Selective cross-coupling of allylic silanolate salts with aromatic bromides using trialkylphosphonium tetrafluoroborate salts prepared directly from phosphine•borane adducts

Scott E. Denmark, Nathan S. Werner

Research output: Contribution to journalArticlepeer-review

Abstract

The γ-selective, palladium-catalyzed cross-coupling of sodium (Z)-2-butenyldiethylsilanolate with a variety of aromatic bromides is reported. The protocol provides high yields (73-94%) and site selectivity (γ/α, 25:1 → > 99:1) in the coupling of electron-rich, electron-poor, sterically hindered, and heteroaromatic bromides. The use of a configurationally homogeneous (Z)-silanolate, nontransferable ethyl groups, and a sterically bulky trialkylphosphonium tetrafluoroborate salt (t-BuCy 2PH +BF 4 -) prepared directly from the corresponding air-stable phosphine•borane adduct are critical to the success of the method.

Original languageEnglish (US)
Pages (from-to)4596-4599
Number of pages4
JournalOrganic Letters
Volume13
Issue number17
DOIs
StatePublished - Sep 2 2011

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'γ-Selective cross-coupling of allylic silanolate salts with aromatic bromides using trialkylphosphonium tetrafluoroborate salts prepared directly from phosphine•borane adducts'. Together they form a unique fingerprint.

Cite this