Copper-Catalyzed 6-endo-dig O-Cyclization of 2-(But-3-en-1-yn-1-yl)benzamide

Abstract

The copper-catalyzed synthesis of 3-vinylisocoumarin-1-imine is reported. The transformation proceeds smoothly with good yields in THF and the regioselectivity was determined by a O-nucleo­philic 6-endo cyclization. Studies on the mechanism indicate that copper trifluoroacetate serves as a Lewis acid, and the use of vinyl-connected 2-alkynylbenzamide is important for this O-nucleophilic 6-endo cyclization.

Key words

copper catalysis - O-nucleophilic 6-endo cyclization - Lewis acid - vinyl-connected 2-alkynylbenzamide - isocoumarin

• References


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• 11 CCDC 1941980 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.