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Synthesis of 1,4‐bis(4‐pyridyl)butadiyne
Author(s) -
Ciana Leopoldo Delia,
Haim Albert
Publication year - 1984
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.5570210268
Subject(s) - chemistry , diethylamine , triphenylphosphine , yield (engineering) , medicinal chemistry , toluene , pyridine , sodium hydroxide , copper , methyl iodide , palladium , chloride , iodide , oxidative coupling of methane , polymer chemistry , organic chemistry , catalysis , materials science , metallurgy
2‐Methyl‐4‐(4‐pyridyl)‐3‐butyn‐2‐ol ( 2 ) was prepared in 70% yield by the reaction of 4‐bromopyridine with 2‐methyl‐3‐butyn‐2‐ol in diethylamine in the presence of bis(triphenylphosphine)palladium(II) chloride and copper(I) iodide. Removal of the protective group in 2 by refluxing with sodium hydroxide in toluene yields (90%) 4‐ethynylpyridine ( 3 ). Oxidative coupling of 3 in pyridine by dioxygen in the presence of copper(I) chloride produces a 92% yield of 1,4‐bis(4‐pyridyl)butadiyne.