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Synfacts 2006(1): 0088-0088  
DOI: 10.1055/s-2005-921703
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Microwave-Assisted Solid-Phase Dötz Benzannulation Reaction

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Tomohiko Beppu
M. Shanmugasundaram, I. Garcia-Martinez, Q. Li, A. Estrada, N. E. Martinez, L. E. Martinez*
University of Texas at El Paso, USA
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Publication History

Publication Date:
16 December 2005 (online)

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Significance

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.