Abstract
A microwave-assisted solid-phase Dötz benzannulation reaction using a resin-bound chromium carbene complex was demonstrated. The cyclization of Wang resin-supported Fischer carbene complex 1 with various alkynes 2 followed by subsequent treatment with cerium(IV) ammonium nitrate (CAN) gave naphthoquinone derivatives 4 in moderate yields without the formation of indenes, indenones or cyclobutenones as side products. The reaction of 1,4-diphenyl butadiyne (R1 = Ph, R2 = C≡CPh) with 1 cleanly afforded the mono benzannulation product 4 (R1 = Ph, R2 = C≡CPh) in 68% yield without any intermolecular double benzannulations or cyclobutenone formation.
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