Discovery of a tetraarylhydrazine catalyst for electrocatalytic synthesis of imidazo-fused N-heteroaromatic compounds

Autor:	Zhong-Yi Mao, Zhong-Wei Hou, Hai-Chao Xu
Rok vydání:	2021
Předmět:	Tris Annulation Electrolysis Organic Chemistry Hydrazine Electrocatalyst Biochemistry Combinatorial chemistry law.invention Catalysis chemistry.chemical_compound chemistry law Intramolecular force Amine gas treating Physical and Theoretical Chemistry
Zdroj:	Organic & Biomolecular Chemistry. 19:8789-8793
ISSN:	1477-0539 1477-0520
DOI:	10.1039/d1ob01644j
Popis:	The development of electrocatalytic synthetic methods hinges on efficient molecular catalysts. Triarylamines are well-known redox catalysts because of the good stability of their corresponding amine radical cations. Herein we show that tris(4-(tert-butyl)phenyl)amine decomposes unexpectedly during electrolysis in MeOH/THF to afford a tetraarylhydrazine, 1,1,2,2-tetrakis(4-(tert-butyl)phenyl)hydrazine. In addition, we have applied this tetraarylhydrazine, which is either preprepared or formed in situ from tris(4-(tert-butyl)phenyl)amine, as an electrocatalyst for the synthesis of imidazopyridines and related N-heteroaromatic compounds through intramolecular [3 + 2] annulation. This metal-free electrocatalytic method provides straightforward access to the N-heteroaromatic compounds from readily available materials without the need for external chemical oxidants.
Databáze:	OpenAIRE
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