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

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

Journal Name: Current Organic Chemistry

Volume 16 , Issue 12 , 2012

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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.

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

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Article Details

VOLUME: 16
ISSUE: 12
Year: 2012
Page: [1540 - 1548]
Pages: 9
DOI: 10.2174/138527212800672538
Price: $58

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