Suzuki−Miyaura coupling reactions of iodo(difluoroenol) derivatives, fluorinated building blocks accessible at near-ambient temperatures

Peter G Wilson, Jonathan M Percy, Joanna Redmond, Adam W. McCarter

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

A recently developed method for the nearambient generation of difluorovinylzinc reagents has facilitated the preparation of 1-(N,N-diethylcarbamoyloxy)-2,2-difluoro-1 - i o d o e t h e n e and 2 , 2 - d i fl u o r o - 1 - i o d o - 1 - ( 2 ′ -
methoxyethoxymethoxy)ethene. The utility of these reagents has been investigated in Suzuki−Miyaura couplings with a range of potassium trifluoroborate coupling partners, with the scope of successful couplings proving wide. Deiodinated species appeared as significant side products, but a solvent change from i-PrOH to t-BuOH suppressed the pathway to these species and improved coupling yields.
Original languageEnglish
Pages (from-to)6384-6393
Number of pages10
JournalJournal of Organic Chemistry
Volume77
Issue number15
DOIs
Publication statusPublished - 3 Aug 2012

Keywords

  • coupling yields
  • Suzuki–Miyaura couplings
  • potassium trifluoroborate
  • solvents

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