Practical synthesis of 6-aryluridines via palladium(II) acetate catalyzed Suzuki–Miyaura cross-coupling reaction

• Published in: Tetrahedron Vol. 67; no. 21; pp. 3915 - 3923
• Main Authors: Shih, Yu-Chiao, Chien, Tun-Cheng
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 27.05.2011; Elsevier
• Subjects: Boronic acid; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry, Organic; Cross-coupling; Exact sciences and technology; General and physical chemistry; Nucleoside; Nucleosides, nucleotides and oligonucleotides; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Suzuki–Miyaura; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Uridine; Uridine; Nucleoside; Boronic acid; Suzuki–Miyaura; Cross-coupling; RNA; OLIGONUCLEOTIDES; BASE-PAIRS; FLUORESCENCE; DNA; PYRIMIDINE NUCLEOSIDES; ENZYMATIC INCORPORATION; Suzuki-Miyaura; LITHIATION; DERIVATIVES; Catalytic reaction; Tertiary phosphine; Ligand; Oside; Phosphorus Organic compounds; Suzuki coupling; Suzuki-Miyaura cross-coupling; Cross reaction; Sodium carbonate; Boron Organic compounds; Chemical synthesis; Palladium II Acetate; Protection; Boronic acids; Catalyst
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.03.051

Sugar-protected 6-halouridine derivatives underwent Suzuki–Miyaura cross-coupling reactions with arylboronic acids in the presence of palladium(II) acetate as a catalyst, triphenylphosphine as a ligand, and sodium carbonate as a base. This methodology is applicable to both the C5- and C6-position of uridine and provides a direct access for versatile uridine derivatives. [Display omitted]