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.
Creators(s): |
Buchanan, Helena S. ![]() ![]() ![]() ![]() ![]() ![]() | Item type: | Article |
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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: | 01 Mar 2021 01:48 |
Related URLs: | |
URI: | https://strathprints.strath.ac.uk/id/eprint/61338 |
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