Premium
Indium Tribromide Catalyzed Coupling Reaction of Enol Ethers with Silyl Ketene Imines toward the Synthesis of β,γ‐Unsaturated Nitriles
Author(s) -
Nishimoto Yoshihiro,
Nishimura Takashi,
Yasuda Makoto
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503414
Subject(s) - ketene , silylation , enol , chemistry , catalysis , organic chemistry , indium , coupling reaction , photochemistry , medicinal chemistry
Herein, a coupling reaction of enol ethers with silyl ketene imines in the presence of catalytic amounts of InBr 3 and Me 3 SiBr is described. Kinetic studies have revealed that an indium catalyst and Me 3 SiBr accelerated the coupling process and the regeneration of the catalyst, respectively. Various types of enol ethers and silyl ketene imines are applicable. In addition, a formal synthesis of verapamil was achieved by using this novel coupling reaction.