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Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes.

Journal of the American Chemical Society (2013-03-13)
Stepan Chuprakov, Sen Wai Kwok, Valery V Fokin
RÉSUMÉ

Readily available 1-mesyl-1,2,3-triazoles are efficiently converted into a variety of imidazolones and thiazoles by Rh(II)-catalyzed denitrogenative reactions with isocyanates and isothiocyanates, respectively. The proposed triazole-diazoimine equilibrium results in the formation of highly reactive azavinyl metal-carbenes, which react with heterocumulenes causing an apparent swap of 1,2,3-triazole core for another heterocycle.

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Rhodium, powder, 99.95% trace metals basis