One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines

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Abstract

The Au(III)-catalyzed cyclization of 2-alkynylanilines was combined in a one-pot procedure with the Au(I)-catalyzed C3-selective direct alkynylation of indoles using the benziodoxolone reagent TIPS-EBX to give a mild, easy and straightforward entry to 2-substituted-3-alkynylindoles. The reaction can be applied to unprotected anilines, was tolerant to functional groups and easy to carry out (RT, and requires neither an inert atmosphere nor special solvents).

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Brand, J. P., Chevalley, C., & Waser, J. (2011). One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines. Beilstein Journal of Organic Chemistry, 7, 565–569. https://doi.org/10.3762/bjoc.7.65

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