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

Hayao Matsuhashi, Yasuo Hatanaka, Manabu Kuroboshi, Tamejiro Hiyama

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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
JournalHeterocycles
Volume42
Issue number1
Publication statusPublished - 1996
Externally publishedYes

Fingerprint

Pyrimidine Nucleosides
Deoxyuridine
Palladium
Derivatives
Cross Reactions
5-iodouracil
1,3-dimethyluracil
5-iodouridine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of 5-substituted pyrimidine nucleosides through a palladium-catalyzed cross-coupling of alkenylhalosilanes. / Matsuhashi, Hayao; Hatanaka, Yasuo; Kuroboshi, Manabu; Hiyama, Tamejiro.

In: Heterocycles, Vol. 42, No. 1, 1996, p. 375-384.

Research output: Contribution to journalArticle

Matsuhashi, Hayao ; Hatanaka, Yasuo ; Kuroboshi, Manabu ; Hiyama, Tamejiro. / Synthesis of 5-substituted pyrimidine nucleosides through a palladium-catalyzed cross-coupling of alkenylhalosilanes. In: Heterocycles. 1996 ; Vol. 42, No. 1. pp. 375-384.
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