Indium Tribromide Catalyzed Coupling Reaction of Enol Ethers with Silyl Ketene Imines toward the Synthesis of β,γ‐Unsaturated Nitriles | Zendy

Nishimoto Yoshihiro | Zendy; Nishimura Takashi | Zendy; Yasuda Makoto | Zendy

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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.

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