Synthesis of 5-substituted pyrimidine nucleosides through a palladium-catalyzed cross-coupling of alkenylhalosilanes

Hayao Matsuhashi, Yasuo Hatanaka, Manabu Kuroboshi, Tamejiro Hiyama

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Palladium-catalyzed cross-coupling of alkenylhalosilanes with 5-iodouracil and 5-iodouridine derivatives was described. 5-Iodo-1,3-dimethyluracil coupled with alkenylfluorodimethylsilanes to give the corresponding cross-coupled products in good yield. Fully protected 5-iodo-2′-deoxyuridine derivative also underwent the cross-coupling reaction. Noteworthy is that unprotected 5-iodo-2′-deoxyuridine could be converted into the corresponding cross-coupled products in good yields using alkenyl(difluoro)methylsilanes.

Original languageEnglish
Pages (from-to)375-384
Number of pages10
Issue number1
Publication statusPublished - 1996
Externally publishedYes


ASJC Scopus subject areas

  • Organic Chemistry

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