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

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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.

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