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Friedel–Crafts β‐Silylvinylations
Author(s) -
Yamaguchi Masahiko,
Kido Yoshiyuki,
Hayashi Akio,
Hirama Masahiro
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.199713131
Subject(s) - electrophile , cationic polymerization , carbon atom , friedel–crafts reaction , chemistry , organic chemistry , stereochemistry , medicinal chemistry , ring (chemistry) , catalysis
Novel vinylgallium intermediates occur in the β‐silylvinylation of aromatic hydrocarbons with trimethylsilylacetylene in the presence of GaCl 3 at −78°C (see below). The interaction of silylacetylene and GaCl 3 initially generates a highly electrophilic cationic species, which is attacked by arenes at the β‐carbon atom. L Cl, Me.
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