A series of C-5 heteroaryl-2’-deoxyuridines were synthesized from 5-iodo-2’-deoxyuridine. Palladium catalyzed coupling with heteroarylstannanes proved to be a convenient and general method of preparation. Oligonucleotides containing pyridine-, thiophene-, thiazole-, and imidazole-substituted 2’-deoxyuridine analogs gave enhanced thermal stability to complementary RNA relative to thymidine. Thermal denaturation studies showed that oligodeoxynucleotides (ODNs) containing 5-(thiazol-2-yl)-2’-deoxyuridine exhibit the highest thermal denaturation (Tm) and therefore may increase the potency of these ODNs to inhibit gene expression in a sequence specific manner.