Dehydrogenative [4 + 2] Annulation of 1-Indanones with Alkynes Enabled by In-Situ-Generated Nickel Hydride.

A practical and effective nickel-catalyzed dehydrogenative [4 + 2] annulation of 1-indanones with alkynes was reported. In this protocol, nickel-catalyzed desaturation of 1-indanones and nickel hydride catalyzed coupling with alkynes were first incorporated. A cyclopentadiene-type nickel hydride species was generated in situ via β-H elimination, and they subsequently reacted with a wide variety of alkynes to afford various benzo[a]fluorenone derivatives in good yields and regioselectivity.