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Rate Enhancement of the Pauson–Khand Reaction by Primary Amines
Author(s) -
Sugihara Takumichi,
Yamada Mamiko,
Ban Hitoshi,
Yamaguchi Masahiko,
Kaneko Chikara
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199728011
Subject(s) - cyclohexylamine , pauson–khand reaction , yield (engineering) , chemistry , solvent , aqueous solution , primary (astronomy) , medicinal chemistry , reaction rate , mathematics , organic chemistry , catalysis , materials science , physics , astronomy , metallurgy
Two economical and practical sets of conditions have been developed for the Pauson–Khand reaction on the basis that primary amines accelerate this reaction. One method employs more than three equivalents of cyclohexylamine in 1,2‐dichloroethane at 83°C, whereas the other requires a mixed solvent of 1,4‐dioxane and 2 m aqueous NH 3 (1/3 v/v) at 100°C. Under these conditions, for instance, the cylization shown below is complete in 5 or 15 minutes, respectively, and the product is isolated in 99 or 93% yield, respectively.