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

27 Citations (Scopus)

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.
LanguageEnglish
Pages2591-2599
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Volume2000
Issue number16
Early online date26 Jul 2000
DOIs
Publication statusPublished - 2000

Fingerprint

Phosphotyrosine
Iodobenzenes
Copper
Boronic Acids
Organophosphonates
Palladium
Iodides
Organometallics
Scaffolds
Catalysis
Zinc
Phosphates
stannane

Keywords

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

Cite this

Cockerill, G Stuart ; Easterfield, Howard J ; Percy, Jonathan ; Pintat, Stephanie. / Facile syntheses of building blocks for the construction of phosphotyrosine mimetics. In: Journal of the Chemical Society, Perkin Transactions 1. 2000 ; Vol. 2000, No. 16. pp. 2591-2599.
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Facile syntheses of building blocks for the construction of phosphotyrosine mimetics. / Cockerill, G Stuart; Easterfield, Howard J; Percy, Jonathan; Pintat, Stephanie.

In: Journal of the Chemical Society, Perkin Transactions 1, Vol. 2000, No. 16, 2000, p. 2591-2599.

Research output: Contribution to journalArticle

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T1 - Facile syntheses of building blocks for the construction of phosphotyrosine mimetics

AU - Cockerill, G Stuart

AU - Easterfield, Howard J

AU - Percy, Jonathan

AU - Pintat, Stephanie

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N2 - 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.

AB - 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.

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KW - organometallic coupling

KW - boronic acid

KW - scaffolds

KW - facile syntheses

KW - building blocks

KW - construction

KW - phosphotryrosine

KW - mimetics

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