Reagent-Free C-H/N-H Cross-Coupling: Regioselective Synthesis of N-Heteroaromatics from Biaryl Aldehydes and NH3

Huai-Bo Zhao; Zhan-Jiang Liu; Jinshuai Song; Hai-Chao Xu

doi:10.1002/anie.201707192

Reagent-Free C-H/N-H Cross-Coupling: Regioselective Synthesis of N-Heteroaromatics from Biaryl Aldehydes and NH₃

Angew Chem Int Ed Engl. 2017 Oct 2;56(41):12732-12735. doi: 10.1002/anie.201707192. Epub 2017 Sep 8.

Authors

Huai-Bo Zhao¹, Zhan-Jiang Liu¹, Jinshuai Song², Hai-Chao Xu¹

Affiliations

¹ iChEM, State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, P. R. China.
² Fujian Institute of Research on Structure of Matter, Chinese Academy of Sciences, Fuzhou, 350002, P. R. China.

PMID: 28815829
DOI: 10.1002/anie.201707192

Abstract

An unprecedented synthesis of N-heteroaromatics from biaryl aldehydes and NH₃ through reagent-free C-H/N-H cross-coupling has been developed. The electrosynthesis uses NH₃ as an inexpensive and atom-economic nitrogen donor, requires no oxidizing agents, and allows efficient and regioselective access to a wide range of phenanthridines and structurally related polycyclic N-heteroaromatic products.

Keywords: ammonia; cross-coupling; electrochemistry; heterocycles; radicals.

Publication types

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