We describe the first report of the generation of 6, 7-dehydrobenzofuran (6, 7- benzofuranyne) from 6, 7-dihalobenzofurans via metal–halogen exchange and elimination, in a manner similar to our previous work with 6, 7-indole arynes. This benzofuranyne undergoes highly regioselective Diels–Alder cycloadditions with 2-substituted furans.
