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Synlett 1995; 1995(8): 823-824
DOI: 10.1055/s-1995-5084
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The Palladium-Catalysed Carbonylative Coupling of 5-(Trimethylsilylethynyl)-3’,5’-di-O-acetyl-2’-deoxyuridine and 1-Alkynes with Aryl Iodides

Antonio Arcadi, Sandro Cacchi* , Fabio Marinelli, Paola Pace, Gianluca Sanzi
  • *Dipartimento di Chimica, Ingegneria Chimica e Materiali, Università degli Studi, V. Vetoio, località Coppito, I-67100 L’Aquila, Italy
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Publication History

Publication Date:
31 December 2000 (online)

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The palladium-catalysed reaction of 5-(trimethylsilylethynyl)-3’,5’-di-O-acetyl-2’-deoxyuridine with aryl iodides in the presence of n-Bu4NF and triethylamine under a balloon of carbon monoxide produces 5-(2-acylethynyl)-3’,5’-di-O-acetyl-2’-deoxyuridines in good yields at room temperature. The methodology has been extended to the preparation of α,β-ynones from 1-alkynes and aryl iodides.

5-Substituted Uridines - Palladium Catalysis - α,β-Ynones - 1-Alkynes - Silylalkynes