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Investigation of the Carboxylate Position during the Acylation Reaction Catalyzed by Biaryl DMAP Derivatives with an Internal Carboxylate
Author(s) -
Nishino Reiko,
Furuta Takumi,
Kan Keizo,
Sato Makoto,
Yamanaka Masahiro,
Sasamori Takahiro,
Tokitoh Norihiro,
Kawabata Takeo
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201300665
Subject(s) - carboxylate , acylation , pyridine , chemistry , catalysis , combinatorial chemistry , medicinal chemistry , organic chemistry
Location of the carboxylate ion : A series of biaryl DMAP catalysts with an internal carboxylate was prepared, and the catalytic activities of the derivatives were evaluated to determine the carboxylate position that most accelerated the DMAP‐catalyzed acylation. The carboxylate ion proximal to the pyridine ring in a face‐to‐face geometry was found to act as an effective general base for the acylation reaction.