Regioselectivity-Switchable Intramolecular Hydroarylation of Ynone

摘要

The switchable catalytic approach to the regioselective intramolecular hydroarylation of ynone has been developed. When ZnI2 was used as catalyst, the umpolung alpha-arylation of ynone was realized via an addition-elimination process of iodine ion to generate the ortho-phenanthrenequinone methide (o-PQM), which could be trapped by styrene to form benzo[f,h]chromenes through hetero-Diels-Alder reaction. While IPrAuCl/AgSbF6 was applied, however, the beta-arylation of ynone took place to afford benzocycloheptene-5-ones in moderate to excellent yields.

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