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Copper-Catalyzed Tandem C[BOND]C/C[BOND]O Bond-Forming Reactions of ortho-Halo-β-chlorostyrenes with Ketones: Synthesis of 4-Trifluoromethylbenzoxepines

Authors

  • Lei-Lei Sun,

    1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Fax: (+86)-577-8668-9615; phone: (+86)-577-8668-9615
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  • Bo-Lun Hu,

    1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Fax: (+86)-577-8668-9615; phone: (+86)-577-8668-9615
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  • Ri-Yuan Tang,

    1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Fax: (+86)-577-8668-9615; phone: (+86)-577-8668-9615
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  • Chen-Liang Deng,

    1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Fax: (+86)-577-8668-9615; phone: (+86)-577-8668-9615
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  • Xing-Guo Zhang

    Corresponding author
    1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Fax: (+86)-577-8668-9615; phone: (+86)-577-8668-9615
    • College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Fax: (+86)-577-8668-9615; phone: (+86)-577-8668-9615
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Abstract

A copper-catalyzed cyclization reaction of trifluoromethyl-containing ortho-halo-β-chlorostyrenes with ketones has been developed. Using a combination of copper(I) bromide, 2,2,6,6-tetramethylheptane-3,5-dione and sodium tert-butoxide, a variety of 4-trifluoromethylbenzoxepines was prepared in moderate to good yields by the tandem α-alkenylation of ketones with subsequent O-arylation.

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