The hexadehydro-Diels–Alder reaction

Thomas Hoye, Beeraiah Baire, Dawen Niu, Patrick Willoughby and Brian Woods
DOI: 10.1038/nature11518

This isn’t the first time a [4+2] alkyne-diyne cycloaddition has been reported, but the reaction is remarkable in that this approach to reactive arynes hasn’t been widely exploited before now. Hoye and coworkers have devised a simple intramolecular hexadehydro-Diels-Alder reaction, which proceeds at relatively low temperature or without a lewis acid. The aryne adducts are trapped with a variety of reactive tethers.

Clearly this chemistry can prepare complex polycyles very quickly form acyclic precursors. I wonder if it will find wide use in synthesis.


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