Organocatalytic γ′[C(sp³)–H] Functionalization of Ynones: An Unusual Approach for the Cyclopentannulation of Benzothiophenes

Abstract

An efficient organocatalytic approach for the cyclopenta[b]annulation of benzothiophenes via γ′[C(sp³)–H] functionalization of ynones is described. Nucleophilic addition of an organophosphine to the designed ynones generates heteroaryl-based ortho-quinodimethanes (oQDMs), which undergo carbocyclization to provide a variety of cyclopenta-fused benzothiophenes. This approach also constitutes an unusual organophosphine-catalyzed intramolecular hydroalkylation of ynones.

Key words

organophosphines - hydroalkylation - cyclopentannulation - ynones - benzothiophenes

• References

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