Facile syntheses of building blocks for the construction of phosphotyrosine mimetics

G Stuart Cockerill, Howard J Easterfield, Jonathan Percy, Stephanie Pintat

Research output: Contribution to journalArticle

28 Citations (Scopus)
236 Downloads (Pure)

Abstract

The copper-catalysed zinc phosphonate chemistry described by Yokomatsu and Shibuya can be used to enter the classical organometallic coupling repertoire via Stille and Suzuki–Miyaura couplings. 1,4-Diiodobenzene underwent coupling with the organozinc reagent derived from diethyl bromodifluoromethylphosphonate with copper(I) catalysis to afford diethyl (4-iodophenyl)difluoromethylphosphonate. Higher yielding couplings were run with (4-trifluoromethylsulfonyloxy)- and (4-nonafluorobutylsulfonyloxy)-iodobenzenes. The iodide and the triflate coupled under palladium-catalysed conditions with a range of stannanes and boronic acids in moderate to excellent yields. Shibuya–Yokomatsu couplings were also successful with more functionalised iodoarenes and heteroarenes presenting the important phosphate mimic on a range of scaffolds.
Original languageEnglish
Pages (from-to)2591-2599
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Volume2000
Issue number16
Early online date26 Jul 2000
DOIs
Publication statusPublished - 2000

Keywords

  • zinc phosphonate
  • organometallic coupling
  • boronic acid
  • scaffolds
  • facile syntheses
  • building blocks
  • construction
  • phosphotryrosine
  • mimetics

Fingerprint Dive into the research topics of 'Facile syntheses of building blocks for the construction of phosphotyrosine mimetics'. Together they form a unique fingerprint.

Cite this