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Functionalization of Alkynes Catalyzed by t ‐Bu‐P4 Base
Author(s) -
Imahori Tatsushi,
Hori Chieko,
Kondo Yoshinori
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404076
Subject(s) - phenylacetylene , chemistry , nucleophile , phosphazene , base (topology) , catalysis , acetylide , superbase , medicinal chemistry , enol , enyne , surface modification , organic chemistry , mathematical analysis , mathematics , polymer
The addition of O‐ and N‐nucleophiles to alkynes catalyzed by a phosphazene base, t ‐Bu‐P4 base, was investigated. Alkynes were easily transformed to enol ethers and enamines in DMSO by the addition of nucleophiles. When phenylacetylene was reacted with diisopropylamine, a unique head‐to‐head dimerization of phenylacetylene was observed to give the enyne derivative. Terminal proton of phenylacetylene was also catalytically activated by t ‐Bu‐P4 base to generate the acetylide anion which was reacted with carbonyl compounds to give phenylpropargylic alcohol derivatives.