Abstract
Following our previous results on an environmentally benign one-pot Sonogashira-cyclization protocol to obtain substituted furopyrimidine nucleosides under aqueous conditions, we investigate herein the Suzuki-Miyaura cross-coupling reactions of aryl and heteroaryl derivatives at the C5 position of unprotected 2'-deoxyuridine in the same media with a common catalyst system avoiding exotic ligands, since palladium acetate and triphenylphosphine afforded the expected products in moderate to good yields.
Highlights
Nucleosides attract attention due to the central role they play in all living systems
To the best of our knowledge, only two examples in the 5-iodouridine [41,42] and one in the 2'-deoxyuridine [43] series are reported in the literature where the experimental conditions required either tris(3-sulfonatophenyl)phosphine trisodium salt (TPPTS) as a specific ligand or palladium supported on reverse phase glass beads
Based on our interest in environmentally sound processes [44,45], we investigated the development of a Suzuki-Miyaura reaction with 2'-deoxyuridines in a completely aqueous medium using a readily available and inexpensive catalyst/ligand system
Summary
Nucleosides attract attention due to the central role they play in all living systems. To the best of our knowledge, only two examples in the 5-iodouridine [41,42] and one in the 2'-deoxyuridine [43] series are reported in the literature where the experimental conditions required either tris(3-sulfonatophenyl)phosphine trisodium salt (TPPTS) as a specific ligand or palladium supported on reverse phase glass beads. This induced us to disclose a similar straightforward method as a natural extension of the current available methods. Based on our interest in environmentally sound processes [44,45], we investigated the development of a Suzuki-Miyaura reaction with 2'-deoxyuridines in a completely aqueous medium using a readily available and inexpensive catalyst/ligand system
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