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Paper | Special issue | Vol 90, No. 2, 2015, pp.939-949
Published online, 18th August, 2014
DOI: 10.3987/COM-14-S(K)59
Rhodium-Catalyzed 2-Methylthiolation Reaction of Thiazoles/Oxazoles Using 2-(Methylthio)thiazole

Mieko Arisawa,* Yuri Nihei, and Masahiko Yamaguchi*

*Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, sendai 980-8578, Japan


RhH(PPh3)4 and 1,3-bis(dicyclohexyl)phosphinopropane (dcypp) catalyze the 2-methylthiolation of oxazoles and thiazoles using 2-(methylthio)thiazole as a thiolating reagent. The methylthio transfer reaction is under equilibrium, and various 2-methylthiolated thiazoles and oxazoles were obtained in moderate to good yields by removing thiazole under refluxing o-dichlorobenzene.