Journal
ORGANIC LETTERS
Volume 14, Issue 2, Pages 468-471Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol2029993
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- Deutsche Forschungsgemeinschaft (DFG) [Li 597/5-1]
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Treatment of mono- and nonbrominated 2-acylpyrroles with Selectfluor under microwave conditions leads to fluorination of the pyrrole ring in the 5-position. In particular, 2-trichloroacetylated pyrrole can be fluorinated. As an example, dihydrofluorohymenidin was synthesized and dehydrogenated to fluorohymenidin as the first fluorinated pyrrole-imidazole alkaloid. Introduction of the vinyl double bond was achieved by chlorination of the 2-aminoimidazole moiety, followed by dehydrochlorination at 100 degrees C in DMF.
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