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
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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