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Metal-Free C-H Amination for Indole Synthesis

Young Ho Jang and So Won Youn*

*Center for New Directions in Organic Synthesis, Department of Chemistry and Research Institute for Natural Sciences, Hanyang University, Seoul 133-791, Korea, Email: sowony73hanyang.ac.kr

Y. H. Jang, S. W. Youn, Org. Lett., 2014, 16, 3720-3723.

DOI: 10.1021/ol5015398  (free Supporting Information)


Abstract

The use of DDQ as an oxidant enables an effective metal-free C-H amination of N-Ts-2-alkenylanilines to afford a diverse range of substituted indoles. This operationally simple and robust protocol obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.

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Key Words

indoles, DDQ


ID: J54-Y2014