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Copper(I) Chloride‐Catalyzed Three‐Component Coupling Reaction of Primary Amines with Electrophiles and α‐Halogen‐Substituted Allylsilanes to Form Unsymmetrical Tertiary Amines
Author(s) -
Kozuka Makoto,
Inoue Akihiko,
Tsuchida Teruko,
Mitani Michiharu
Publication year - 2006
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.200505406
Subject(s) - chemistry , electrophile , alkyl , halogen , halide , catalysis , coupling reaction , organic chemistry , medicinal chemistry , chloride , polymer chemistry
Abstract Tertiary amines with three different substituents, in one of which a vinylsilane functionality was included, were straightforwardly formed by the copper(I) chloride‐catalyzed tandem reaction of primary amines, α‐halogen‐substituted allylsilanes, and electrophiles such as electron‐deficient olefins, alkyl halides, alkyl tosylates, or epoxides. In the case using electron‐deficient olefins as the electrophile, the addition of chloroacetone to the reaction system afforded the three‐component coupling reaction more effectively. The addition of trimethyl borate as a co‐catalyst improved the yields of the three‐component coupling products in the reaction using alkyl halides, alkyl tosylates, or epoxides as the electrophiles, although the reaction times were lengthened.