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 (https://doi.org/10.1021/acs.orglett.7b01602)

[thumbnail of Buchanan-etal-OL-2017-Modular-step-efficient-palladium-catalyzed-cross-coupling-strategy]
Preview
 Text. Filename: Buchanan_etal_OL_2017_Modular_step_efficient_palladium_catalyzed_cross_coupling_strategy.pdf
Final Published Version
License: Creative Commons Attribution 4.0 logo
Download (1MB)| Preview

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.

CORE (COnnecting REpositories)