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5‐Vinylpyrimidines. Synthesis via organopalladium intermediates
Author(s) -
Arai Isamu,
Daves G. Doyle
Publication year - 1978
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570150240
Subject(s) - organopalladium , chemistry , palladium , regioselectivity , triphenylphosphine , double bond , medicinal chemistry , catalysis , vinyl acetate , organic chemistry , polymer , copolymer
Reactions of 1,3‐dimethyl‐5‐iodouracil or 2,4‐dimethoxy‐5‐iodopyrimidine with vinyl acetate in the presence of a catalytic amount of diacetato‐ bis (triphenylphosphine) palladium (II) resulted in good yields of the corresponding 5‐vinylpyrimidines. The reactions are viewed as resulting from regioselective addition of an initially formed 5‐pyrimidinyl palladium species to the double bond of vinyl acetate followed by elimination of a palladium acetate with regeneration of the double bond and formation of the 5‐vinylpyrimidine product.