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

Buchanan, Helena S. and Pauff, Steven M. and Kosmidis, Tilemachos D. and Taladriz-Sender, Andrea and Rutherford, Olivia I. and Hatit, Marine Z. C. and Fenner, Sabine and Watson, Allan J. B. and Burley, Glenn A. (2017) Modular, step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides. Organic Letters, 19 (14). pp. 3759-3762. ISSN 1523-7060

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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.

    ORCID iDs

    Buchanan, Helena S. ORCID logoORCID: https://orcid.org/0000-0001-8710-0511, Pauff, Steven M. ORCID logoORCID: https://orcid.org/0000-0002-7499-3207, Kosmidis, Tilemachos D. ORCID logoORCID: https://orcid.org/0000-0001-6194-6092, Taladriz-Sender, Andrea ORCID logoORCID: https://orcid.org/0000-0002-8274-4761, Rutherford, Olivia I. ORCID logoORCID: https://orcid.org/0000-0003-3517-8186, Hatit, Marine Z. C. ORCID logoORCID: https://orcid.org/0000-0002-5713-6596, Fenner, Sabine, Watson, Allan J. B. and Burley, Glenn A.;
    • Item type:Article
      ID code:61338
      Dates:
      Date
      Event
      21 July 2017
      Published
      6 July 2017
      Published Online
      6 July 2017
      Accepted
      Keywords:boron substrates, Sonogashira coupling, Suzuki−Miyaura cross coupling, ribonucleosides, Chemistry, Organic Chemistry
      Subjects:Science > Chemistry
      Department:Faculty of Science > Pure and Applied Chemistry
      Depositing user: Pure Administrator
      Date deposited:24 Jul 2017 15:28
      Last modified:02 Jun 2021 00:36
      Related URLs:
      URI:https://strathprints.strath.ac.uk/id/eprint/61338
    CORE (COnnecting REpositories)