Silyl trifluoromethanesulfonate-activated para-methoxybenzyl methyl ether as an alkylating agent for thiols and aryl ketones

C. Wade Downey*, Sarah E. Covington, Derek C. Obenschain, Evan Halliday, James T. Rague, Danielle N. Confair

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Para-Methoxybenzyl methyl ether acts as an alkylating agent for thiols in the presence of trimethylsilyl trifluoromethanesulfonate and trialkylamine base in good yields (58-96%). Aryl ketones are alkylated under similar conditions, probably through an enol silane intermediate, also in high yields (67-95%). The active alkylating species is likely a p-methoxybenzyl cation.

Original languageEnglish (US)
Pages (from-to)5213-5215
Number of pages3
JournalTetrahedron Letters
Volume55
Issue number37
DOIs
StatePublished - Jul 2005

Keywords

  • Alkylation
  • Enol silanes
  • Methyl ethers
  • Silyl triflates

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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