4.7 Article

HFIP Promoted C3 Alkylation of Lawsone and 4-Hydroxycoumarin with Alcohols by Dehydrative Cross-Coupling

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 16, Pages 10638-10647

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01207

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Funding

  1. Natural Science Foundation of Zhejiang Province [LQ20B020005]

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An environmentally benign system for the direct alkylation of lawsones and 4-hydroxycoumarins with alcohols in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) is reported. The reaction proceeded smoothly via a dehydrative cross-coupling process by utilizing the unique properties of HFIP. A variety of alkylated products and subsequent one-pot cyclized products (pyranonaphthoquinones and pyranocoumarins) could be obtained in 40-93% yields.

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