Considering aryl azides as electrophilic partners for the TosMIC mediated Van Leusen reaction, a novel multicomponent synthesis of 4-tosyl-1-arylimidazoles is reported. In this transformation, two molecules of TosMIC participate in the reaction mechanism in two different ways, with the second molecule undergoing a novel type of fragmentation resulting in the incorporation of a C-H into the final product.
Aryl azides as forgotten electrophiles in the Van Leusen reaction: a multicomponent transformation affording 4-tosyl-1-arylimidazoles / C. Necardo, A.I. Alfano, E. Del Grosso, S. Pelliccia, U. Galli, E. Novellino, MENEGHETTI FIORELLA, M. Giustiniano, G.C. Tron. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 84:24(2019 Dec), pp. 16299-16307.
Aryl azides as forgotten electrophiles in the Van Leusen reaction: a multicomponent transformation affording 4-tosyl-1-arylimidazoles
MENEGHETTI FIORELLA;
2019
Abstract
Considering aryl azides as electrophilic partners for the TosMIC mediated Van Leusen reaction, a novel multicomponent synthesis of 4-tosyl-1-arylimidazoles is reported. In this transformation, two molecules of TosMIC participate in the reaction mechanism in two different ways, with the second molecule undergoing a novel type of fragmentation resulting in the incorporation of a C-H into the final product.
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