Modular, step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides

Helena S. Buchanan, Steven M. Pauff, Tilemachos D. Kosmidis, Andrea Taladriz-Sender, Olivia I. Rutherford, Marine Z. C. Hatit, Sabine Fenner, Allan J. B. Watson, Glenn A. Burley

Research output: Contribution to journalArticle

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Abstract

Two Pd-catalyzed methods to access 6-heteroaryl 2-aminopurine ribonucleosides from 6-chloroguanosine are described. First, Pd-132-catalyzed Suzuki-Miyaura cross-coupling using a series of boron substrates and 6-chloroguanosine forms 6-heteroaryl-2-aminopurines in a single step. The versatility of 6-chloroguanosine is further demonstrated using a modified Sonogashira coupling employing potassium iodide as an additive. Finally, the utility of the 6-alkynyl-2-aminopurine ribonucleoside as a dipolarophile in [3 + 2] cycloadditions is presented, affording triazoles and isoxazoles when reacted with azide and isonitrile 1,3-dipoles, respectively.

Original languageEnglish
Pages (from-to)3759-3762
Number of pages4
JournalOrganic Letters
Volume19
Issue number14
Early online date6 Jul 2017
DOIs
Publication statusPublished - 21 Jul 2017

Keywords

  • boron substrates
  • Sonogashira coupling
  • Suzuki−Miyaura cross coupling
  • ribonucleosides

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