Mehdid MA, Djafri A, Andreoli F, Vanthuyne N, Farran D, Niebler J, Büttner A, Giorgi M, Roussel C (2013)
Publication Type: Journal article
Publication year: 2013
DOI: 10.1016/j.tet.2013.04.013
A metal free synthesis of S-alkyl thioesters, which does not involve alkylthiol or thiocarboxylic acid as sulfur source is disclosed. The process involves first an acylation at the nitrogen of the readily available N-(2-aminophenyl)-4-methyl-thiazolin-2-thione, second an alkylation at sulfur of the resulting amides and finally a base catalyzed metathetic reaction, which provides under very mild conditions and in high isolated yields the S-alkyl thioesters. An ion-pair intermediate (9-acyl-3-methyl[1,3]thiazolo[3,2-a][3,1]benzimidazol-9-ium alkylthiolate) accounts for the formation of mixed thioesters during cross-coupling experiments.
S-Alkyl diversity is provided by the alkylating agent and the acyl diversity comes from the acylating agent, while the sulfur atom is provided by the heterocycle.
APA:
Mehdid, M.A., Djafri, A., Andreoli, F., Vanthuyne, N., Farran, D., Niebler, J.,... Roussel, C. (2013). Metathetic Sulfur Transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives: Part III: a new Route to Diversely Substituted S-alkyl thioesters. Tetrahedron. https://doi.org/10.1016/j.tet.2013.04.013
MLA:
Mehdid, Mohammed Amine, et al. "Metathetic Sulfur Transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives: Part III: a new Route to Diversely Substituted S-alkyl thioesters." Tetrahedron (2013).
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