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.
- boron substrates
- Sonogashira coupling
- Suzuki−Miyaura cross coupling
Buchanan, H. S., Pauff, S. M., Kosmidis, T. D., Taladriz-Sender, A., Rutherford, O. I., Hatit, M. Z. C., ... Burley, G. A. (2017). Correction to "Modular, step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides". Organic Letters, 19(14). https://doi.org/10.1021/acs.orglett.7b02273