4.8 Article

Metal-Free C-H Amination for Indole Synthesis

Journal

ORGANIC LETTERS
Volume 16, Issue 14, Pages 3720-3723

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol5015398

Keywords

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Funding

  1. National Research Foundation of Korea (NRF) - Ministry of Education
  2. MSIP [2012R1A1A2041471, 2012M3A7B4049654, 2014-011165]

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An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, 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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