Electrochemical C-H/N-H Functionalization for the Synthesis of Highly Functionalized (Aza)indoles

Zhong-Wei Hou; Zhong-Yi Mao; Huai-Bo Zhao; Yared Yohannes Melcamu; Xin Lu; Jinshuai Song; Hai-Chao Xu

doi:10.1002/anie.201602616

Electrochemical C-H/N-H Functionalization for the Synthesis of Highly Functionalized (Aza)indoles

Angew Chem Int Ed Engl. 2016 Aug 1;55(32):9168-72. doi: 10.1002/anie.201602616. Epub 2016 May 30.

Authors

Zhong-Wei Hou¹, Zhong-Yi Mao¹, Huai-Bo Zhao¹, Yared Yohannes Melcamu¹, Xin Lu², Jinshuai Song^{1

3}, Hai-Chao Xu⁴

Affiliations

¹ Collaborative Innovation Center of Chemistry for Energy Material, State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province and, Department of Chemistry, Xiamen University, Xiamen, 361005, P.R. China.
² Collaborative Innovation Center of Chemistry for Energy Material, State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province and, Department of Chemistry, Xiamen University, Xiamen, 361005, P.R. China. xinlu@xmu.edu.cn.
³ Fujian Institute of Research on Structure of Matter, Chinese Academy of Sciences, Fuzhou, 350002, P.R. China.
⁴ Collaborative Innovation Center of Chemistry for Energy Material, State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province and, Department of Chemistry, Xiamen University, Xiamen, 361005, P.R. China. haichao.xu@xmu.edu.cn.

PMID: 27240116
DOI: 10.1002/anie.201602616

Abstract

Indoles and azaindoles are among the most important heterocycles because of their prevalence in nature and their broad utility in pharmaceutical industry. Reported herein is an unprecedented noble-metal- and oxidant-free electrochemical method for the coupling of (hetero)arylamines with tethered alkynes to synthesize highly functionalized indoles, as well as the more challenging azaindoles.

Keywords: electrochemistry; heterocycles; indoles; radicals; redox chemistry.

Publication types

Research Support, Non-U.S. Gov't