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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.

    Item type:Article
    ID code:61338
    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 Feb 2019 05:42
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/61338
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