Copper(I) Chloride-Catalyzed Three-Component Coupling Reaction of Primary Amines with Electrophiles and α-Halogen-Substituted Allylsilanes to Form Unsymmetrical Tertiary Amines

✍ Scribed by Makoto Kozuka; Akihiko Inoue; Teruko Tsuchida; Michiharu Mitani

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 164 KB
• Volume: 348
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.200505406

✦ Synopsis

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.