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Paper | Special issue | Vol 42, No. 1, 1996, pp.375-384
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S49
Synthesis of 5-Substituted Pyrimidine Nucleosides through a Palladium-catalyzed Cross-Coupling of Alkenylhalosilanes

Hayao Matsuhashi, Yasuo Hatanaka, Manabu Kuroboshi, and Tamejiro Hiyama

*Research Laboratory of Resources Utilization, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan


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.