Dongfeng Zhang, P. Li, Zi-yun Lin
Jan 23, 2014
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Influential Citations
16
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Journal
Synthesis
Abstract
A convenient and efficient synthesis of gem-difluorinated compounds is reported. The synthetic route toward various 2-substituted and 3-substituted 1,1-difluoro-6-nitro-2,3-dihydro-1H-indene derivatives is described starting from commercially available indanone. The key gem-difluorination step is accomplished in good yield by treatment of in situ generated bromine fluoride (BrF) with a dithioketal. A plausible mechanism discussing the competition between substitution and elimination is provided to rationalize the outcome of the reactions of the 3-brominated compounds with different amines.