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A heterogeneous gold(I)-catalyzed cascade annulation of aldehydes with propargylamine leading to 3-substituted 2,5-dimethylpyrazines

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Abstract A heterogeneous gold(I)-catalyzed cascade annulation reaction of aldehydes with propargylamine was achieved in 1,2-dichloroethane at 40 °C by using an MCM-41-immobilized phosphine gold(I) complex[MCM-41-PPh 3 -AuNTf 2 ] as catalyst,… Click to show full abstract

Abstract A heterogeneous gold(I)-catalyzed cascade annulation reaction of aldehydes with propargylamine was achieved in 1,2-dichloroethane at 40 °C by using an MCM-41-immobilized phosphine gold(I) complex[MCM-41-PPh 3 -AuNTf 2 ] as catalyst, yielding a variety of 3-substituted 2,5-dimethylpyrazines in good to excellent yields. The new heterogeneous gold(I) catalyst can easily be prepared via a simple procedure from commercially readily available reagents, and recovered by filtration of the reaction solution and recycled at least eight times without significant loss of activity.

Keywords: cascade annulation; heterogeneous gold; gold; catalyzed cascade; aldehydes propargylamine; gold catalyzed

Journal Title: Journal of Organometallic Chemistry
Year Published: 2017

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