5 years ago

Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products

Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products
David T. Smith, Jon T. Njardarson, Edon Vitaku
A mild dearomatization enabled ortho-selective replacement of an aromatic C–H bond with a hexafluoroacetylacetone (hfacac) substituent has been developed. This reaction is dependent on a hypervalent iodine generated phenoxonium intermediate, a critical choice of solvent, and reagent addition order. The fluorinated dihydrobenzofuran product can be transformed into dihydrobenzofuran and benzofuran products decorated with a 2-trifluoromethyl group. The 3-trifluoromethylacyl substituted benzofurans rapidly form hydrates, which can be reduced to the corresponding alcohols.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01479

DOI: 10.1021/acs.orglett.7b01479

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