Improved microwave-assisted ligand-free Suzuki–Miyaura cross-coupling of 5-iodo-2′-deoxyuridine in pure water

Development of nucleoside analogs under microwave irradiation

“…This cross-coupling reaction involves palladium as catalyst, aryl, alkenyl or alkynyl halides and organoboron [18]. Len et al [19] have also reported the functionalization at the C5 position of 5-iodo-2'-deoxyuridine 32 through ligand free Suzuki-Miyaura reactions in water. Compared with thermal heating, microwave irradiation improves the yield of 33 and decreases the reaction time (Figure 10.5).…”

First Pinacol Coupling in Emulsified Water: Key Role of Surfactant and Impact of Alternative Activation Technologies

“…[20] Indeed, microwave heating has been widely recognized as an efficient tool, and its benefits have been well-documented. [22] Nevertheless,t ot he best of our knowledge, there is no protocol for pinacolc oupling in pure water under microwave heating. [22] Nevertheless,t ot he best of our knowledge, there is no protocol for pinacolc oupling in pure water under microwave heating.…”

Eco-Friendly Physical Activation Methods for Suzuki–Miyaura Reactions

“…Analogues that bear a C-aryl group on the glycone or aglycone section have been more intensively studied. In fact, an easy and efficient procedure for the direct synthesis of 5-aryl-2′-deoxyuridines has been reported, by Gallagher-Duval et al [52], via a ligand-free SMC strategy which starts with totally deprotected 5-iodo-2′-deoxyuridine and different boronic acids and is carried out in pure water. The desired 5-arylated uridine derivatives were synthesized in satisfactory (57%-85%) yields in short reaction times (5-30 min) in the presence of very low Na2PdCl4 Pd catalyst loading amounts (0.05-0.1 mol %) and KOH (0.56 mmol) as the base.…”