Cerium (III) Chloride as a Catalyst in the Clauson-Kaas Reaction: Synthesis and Reactivity of N-Aryl-2-thiocyanatopyrroles

Title:Cerium (III) Chloride as a Catalyst in the Clauson-Kaas Reaction: Synthesis and Reactivity of N-Aryl-2-thiocyanatopyrroles

Volume: 16 Issue: 12

Author(s): Claudio C. Silveira, Margiani P. Fortes and Samuel R. Mendes

Affiliation:

Keywords: Cerium chloride, Clauson-Kaas synthesis, Microwave-assisted reaction, Pyrrol-2-yl disulfides, Pyrrole derivatives, Thiocyanates

Abstract: A new and efficient methodology for the Clauson-Kaas synthesis of N-aryl pyrroles, employing CeCl3.7H2O as catalyst, was developed. The transformation was performed in acetonitrile under reflux, using conventional heating and microwave irradiation. Employing NH4SCN/Oxiall as a new thiocyanating system for the so obtained N-aryl pyrroles, the synthesis 1-aryl-2-thiocyanato-1Hpyrroles was also successfully accomplished. The latter served as starting materials for the high-yielding NaBH4-mediated preparation of 1,2-bis(1-(aryl)-1H-pyrrol-2-yl)disulfides and the phase transfer-mediated synthesis of 1-aryl-2-(trichloromethylthio)-1H-pyrroles.

Cite this article as:

C. Silveira Claudio, P. Fortes Margiani and R. Mendes Samuel, Cerium (III) Chloride as a Catalyst in the Clauson-Kaas Reaction: Synthesis and Reactivity of N-Aryl-2-thiocyanatopyrroles, Current Organic Chemistry 2012; 16 (12) . https://dx.doi.org/10.2174/138527212800672538