The nucleophilic 5-endo-trig cyclization of gem-difluoroolefins with homoallylic functional groups: syntheses of ring-fluorinated dihydroheteroaromatics

Abstract
gem-Difluoroolefins bearing homoallylic tosylamido, hydroxy, or mercapto groups undergo intramolecular nucleophilic substitution of the nitrogen, oxygen, or sulfur with loss of fluorine via a 5-endo-trig process, leading to 2-fluoro-2-pyrrolines, 5-fluoro-2,3-dihydrofurans, or -thiophenes in high yields.

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