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Thionation Using Fluorous Lawesson's Reagent

Zoltán Kaleta, Brian T. Makowski, Tibor Soós,* and Roman Dembinski*

*Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, Email:

Z. Kaleta, B. T Makowski, T. Soos, R. Dembinski, Org. Lett., 2006, 8, 1625-1628.

DOI: 10.1021/ol060208a

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Thionation of amides, 1,4-diketones, N-(2-oxoalkyl)amides, and N,N'-acylhydrazines with the use of a fluorous Lawesson's reagent leads to thioamides, thiophenes, 1,3-thiazoles, and 1,3,4-thiadiazoles in high yields. The isolation of the final products is achieved in most cases by a simple filtration.

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Key Words

Thioamides, Paal-Knorr Thiophene Synthesis, Lawesson's Reagent, Fluorous Phase Organic Synthesis, Thiophenes, 1,3-Thiazoles, 1,3,4-Thiadiazoles

ID: J54-Y2006-1020