Synthesis of 1,4‐bis(4‐pyridyl)butadiyne | Zendy

Ciana Leopoldo Delia | Zendy; Haim Albert | Zendy

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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.

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