KO(t)Bu/DMSO-promoted C-H functionalization of acetylarenes with arylacetylenes (100 °C, 30 min), generating β,γ-ethylenic ketones, triggers upon further heating (100 °C, 4 h, with or without acidifying additive) the cascade assembly of acyl terphenyls and higher polyaromatics in good yields.
Unique
bridgehead nitrones, 8-oxa-6-azabicyclo[3.2.1]oct-6-ene
6-oxides, have been assembled diastereoselectively via acetyldihydropyrans,
products of one-pot self-organization of two molecules of ketones
and two molecules of acetylene, which after oximation undergo acid-catalyzed
ring closure. The proposed mechanism includes the enol double-bond
protonation, followed by intramolecular cyclization involving the
interaction of the carbocation formed with a nitrogen atom. A broad
range of substrates tolerate this facile transformation, in which
the bridgehead nitrones were isolated in high yields.
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