Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Developments in the Reactivity of 2-Methylimidazolium Salts

Developments in the Reactivity of 2-Methylimidazolium Salts
Luisa M. Ferreira, Paula S. Branco, Carlos A. M. Afonso, Gerd Vanhoenacker, Marta C. Corvo, Manoj B. Gawande, Daniela Peixoto, Margarida Figueiredo
Unexpected and unusual reactivity of 2-methylimidazolium salts toward aryl-N-sulfonylimines and aryl aldehydes is here reported. Upon reaction with aryl-N-sulfonylimines, the addition product, arylethyl-2-imidazolium-1-tosylamide (3), is formed with moderate to good yields, while upon reaction with aldehydes, the initial addition product (6) observed in NMR and HPLC–MS experimental analysis is postulated by us as an intermediate to the final conversion to carboxylic acids. Studies in the presence and absence of molecular oxygen allow us to conclude that the imidazolium salts is crucial for the oxidation. A detailed mechanistic study was carried out to provide insights regarding this unexpected reactivity.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00807

DOI: 10.1021/acs.joc.7b00807

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