A Brief and Mild Method for the Generation of Benzofuran-2,3-xylylene in Solution

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Abstract
Benzofuran-2,3-xylylene 3b (2,3-dimethylene-2,3-dihydrobenzofuran) can be generated at -4 °C in acetonitrile by treatment of 2-acetoxymethyl-3-triisopropylsilylmethylbenzofuran (7b), available from 3-methylbenzofuran-2-carboxylic acid dianion (5) in two steps, with tetrabutylammonium fluoride. Trapping the xylylene 3b in situ using reactive Diels-Alder dienophiles gives high yields of the adducts 8 (2-substituted or 2,3-disubstituted 1,2,3,4-tetrahydrodibenzofurans).

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