Abstract: Synthetic electrochemistry may establish direct routes to a preparation of a plethora of organic substances, which are hardly accessible by conventional experimental techniques. Herein, we present an electrochemically-driven method for an assembly of a broad range of rare heterocyclic mesoionic entities –1,2,3-triazole 1-imines. These nitrogen heterocycles were prepared through a transition-metal- and exogenous oxidant-free strategy using a C/Ni electrode pair. Over 30 examples of thus synthesized 1,2,3-triazole 1-imines illustrate selectivity and practical utility of this approach. Key solvent-controlled reactivity patterns for the formation of the triazole imine scaffold were revealed indicating a modulation ability of the developed approach. These experimental findings were additionally justified based on cyclic voltammetry (CV) data and density functional theory (DFT) calculations. Moreover, according to differential scanning calorimetry (DSC) data, some of the prepared 1,2,3-triazole 1-imines correspond to the thermally stable species with an onset decomposition temperature up to 190 °C.

Cite: Shuvaev A. , Feoktistov M. , Teslenko F. , Fershtat L.
Electrochemical Approach Toward Mesoionic 1,2,3‐Triazole 1‐Imines
Advanced Synthesis & Catalysis. 2024. V.366. N24. P.5050-5060. DOI: 10.1002/adsc.202400761 WOS Scopus OpenAlex

Identifiers:

Web of science:	WOS:001329651000001
Scopus:	2-s2.0-85205880284
OpenAlex:	W4401791398

Citing:

DB	Citing
OpenAlex	5
Web of science	4
Scopus	4

Altmetrics: