4.2 Article

RHODIUM-CATALYZED 2-METHYLTHIOLATION REACTION OF THIAZOLES/OXAZOLES USING 2-(METHYLTHIO)THIAZOLE

Journal

HETEROCYCLES
Volume 90, Issue 2, Pages 939-949

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-14-S(K)59

Keywords

Thiazole/Oxazole; Rhodium-Catalyzed Reaction; Equilibrium Reaction; 2-Thiolation Reaction; 2-(Methylthio)thiazole

Funding

  1. Ministry of Education, Culture, Sports, Science and Technology, Japan [21229001]
  2. Asahi Glass Foundation
  3. [22689001]
  4. [25109503]
  5. Grants-in-Aid for Scientific Research [25109503] Funding Source: KAKEN

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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.

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