Partially Fluorinated Heterocycles from 4, 4-Bis (trifluoromethyl)-hetero-1, 3-dienes via C–F Bond Activation–Synthesis of 2-Fluoro-3-(trifluoromethyl) furans

…, B Helmreich, L Hennig, J Spengler, F Albericio…

文献索引：Burger, Klaus; Helmreich, Brigitte; Hennig, Lothar; Spengler, Jan; Albericio, Fernando; Fuchs, Annett Monatshefte fur Chemie, 2007 , vol. 138, # 3 p. 227 - 236

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被引用次数: 8

摘要

Summary. An efficient synthesis of 2-fluoro-3-(trifluoromethyl) furans was developed. Keystep of the reaction sequence is a [4+ 1] cycloaddition reaction of tin (II) chloride to 4, 4- bis (trifluoromethyl)-1-oxabuta-1, 3-dienes. At elevated temperatures the tin heterocycles are transformed into 1-aryl-4, 4-difluoro-3-(trifluoromethyl) but-3-en-1-ones which on treatment with sodium hydride in dry DMF give 2-fluoro-3-(trifluoromethyl) furans. The single fluorine ...