Supported synthesis and functionnalization of 2″-deoxyuridine by Suzuki-Miyaura cross-coupling

The synthesis and modification of 2′-deoxyuridine has been realized under Suzuki-Miyaura palladium-catalyzed cross-coupling conditions. Using Pd(PPh3)4 and Na2CO3, 5-iodo-2′-deoxyuridine bound to solid support is coupled with various boronic acids to give 5-(hetero)aryl-2′-deoxyuridine. Pd(PPh3)4 palladium catalyzed was found to be superior to Pd(OAc)2 and (NHC)Pd(allyl)Cl for Suzuki-Miyaura palladium-catalyzed reactions. Copyright © Taylor & Francis Group, LLC.