Unprecedented formal CH-methylation of aldimines by diazomethane
Тип публікації :
Препринт
Дата випуску :
28 липня 2026 р.
Автор(и) :
Yuliya V. Rassukana
Roman Zakharko
Ludmila Bezgubenko
P. P. ONYS'KO
Alexander B. Rozhenko
Svitlana V. Shishkina
Serhiy V. Ryabukhin
Dmytro M. Volochnyuk
eKNUTSHIR URL :
Журнал :
ChemRxiv
Цитування :
[APA 7] Yuliya, V. R., Roman, Z., Ludmila, B., P., P. O., Alexander, B. R., Svitlana, V. S., Serhiy, V. R., & Dmytro, M. V. (2026). Unprecedented formal CH-methylation of aldimines by diazomethane. ChemRxiv,. https://doi.org/10.26434/chemrxiv.15006654/v1
[ДСТУ] Unprecedented formal CH-methylation of aldimines by diazomethane / V. R. Yuliya та ін. ChemRxiv. 2026. DOI: 10.26434/chemrxiv.15006654/v1 (дата звернення: 11.09.2026).
The formal CH-methylation of aldimines by diazomethane was discovered. The transformation works when at nitrogen atom is EWG group like SOtBu as well as EWG group at C=N bond like CF3, 4-Py, p-C6H4-NO2. Shifting to benzaldehyde derivative leads to stopping of the reaction. Moreover the time of the reaction is strongly dependent from the acceptor power of EWG group at C=N bond. More detailed investigation of the process showed that the reaction proceeds in two steps: (i) triazoline formation via [3+2] cycloaddition; (ii) nitrogen evolution with subsequent proton transfer. Any products of the standard intermediate triazoline decomposition to corresponding aziridine was not observed. Formally we can conclude that the path of the triazoline to ketimine transformation is strongly dependent from the CH-acidity of the corresponding proton from the aldimine.
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