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Paper | Regular issue | Vol 81, No. 4, 2010, pp.965-976
Published online, 10th February, 2010
DOI: 10.3987/COM-10-11906
DDQ-Mediated Tandem Synthesis of Functionalized Pyranocoumarins from 4-Hydroxycoumarins and 1,3-Diarylallylic Compounds

Zhenxing He, Xufeng Lin,* Yuanxun Zhu, and Yanguang Wang

*Department of Chemistry, Zhejiang University , Hangzhou, 310027, China


A simple and efficient DDQ-mediated oxidative cross-coupling between 4-hydroxycoumarin and 1,3-diarylallylic compounds was developed. The reaction furnished functionalized pyranocoumarins in a single step without using any metal catalyst. The tandem process involves an intermolecular C–C bond formation and an intramolecular C–O bond formation through double oxidative C–H activation.