1,3-Dihydro-1,3-bis(benzylidene)isobenzofurans have been prepared in decent yields by heating 1,2-diphenylethynylbenzenes in the presence of copper(I) catalyst. Other products are also observed that do not involve the incorporation of water. The configurationally labile isobenzofuran has been isolated and crystalized in order to determine the geometry of the benzylidene alkenes. Activation of the alkyne by the copper appeares to the key mechanistic step, and the effects of different solvents and metals has been investigated. The presence of two ortho-aldehyde substituents is crucial to the formation of the isobenzofuran; the carbonyl oxygens may coordinate the copper and stabilize the copper-alkyne complex enough to allow its intermolecular reaction with an adventitious water molecule. Substrates with only one ortho-aldehyde moiety do not produce significant quantities of the isobenzofuran products.

1,3-Bis(benzylidene)isobenzofuran synthesis via copper(I) catalyzed hydration of ortho-diynylarenes

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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