Organic Letters
Organic Letters
4 years ago

Modular, Step-Efficient Palladium-Catalyzed Cross-Coupling Strategy To Access C6-Heteroaryl 2-Aminopurine Ribonucleosides

Modular, Step-Efficient Palladium-Catalyzed Cross-Coupling Strategy To Access C6-Heteroaryl 2-Aminopurine Ribonucleosides
Marine Z. C. Hatit, Steven M. Pauff, Olivia I. Rutherford, Andrea Taladriz-Sender, Allan J. B. Watson, Glenn A. Burley, Sabine Fenner, Tilemachos D. Kosmidis, Helena S. Buchanan
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01602

DOI: 10.1021/acs.orglett.7b01602

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