Johannes Niebler - Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives. Part III: An alkylthiol- and thioacid-free route to diversely substituted S-alkyl thioesters

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      Mehdid, M. A., Djafri, A., Andreoli, F., Vanthuyne, N., Farran,   D., Niebler, J., Buettner, A., Giorgi, M., Roussel, C., 2013.   Metathetic sulfur transfer mediated by   N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives. Part   III: An alkylthiol- and thioacid-free route to diversely   substituted S-alkyl thioesters. Tetrahedron 69, 4994-5001.


      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.

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