Electrocatalytic Dehydrogenative Cyclization of 2-Vinylanilides for the Synthesis of Indoles
Yun-Tao Zheng1, Jinshuai Song2, Hai-Chao Xu1
1Key Laboratory of Chemical Biology of Fujian Province, State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. China.
Abstract:
Indole is prevalent in bioactive compounds and natural products. The development of efficient and sustainable methods to access this privileged structural scaffold has been a long-standing interest of synthetic chemists. Herein, we report an electrocatalytic method for the synthesis of indoles through dehydrogenative cyclization of 2-vinylanilides. The reactions employ an organic redox catalyst and do not require any external chemical oxidant, providing speedy and efficient access to 3-substituted and 2,3-disubstituted indoles.
Related Concept Videos
Cycloaddition Reactions: Overview
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Preparation of Nitriles
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism


