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Generation of stereodefined (Z)-3,4-dihydronaphthalen-1(2H)-ones via copper-catalyzed annulation-cyanotrifluoromethylation of 1,7-enynes

A new copper-catalyzed three-component annulation–cyanotrifluoromethylation of 1,7-enynes with Togni’s reagent and TMSCN is reproted, and used to produce stereodefined (Z)-3,4-dihydronaphthalen-1(2H)-ones with a quaternary carbon center in generally good yields. [Display omitted] •A new Cu-catalyzed...

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Bibliographic Details
Published in:Tetrahedron letters 2021-02, Vol.64, p.152722, Article 152722
Main Authors: Ji, Wen-Zhe, Shi, Hao-Nan, Hao, Wen-Juan, Wei, Ping, Tu, Shu-Jiang, Jiang, Bo
Format: Article
Language:English
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Summary:A new copper-catalyzed three-component annulation–cyanotrifluoromethylation of 1,7-enynes with Togni’s reagent and TMSCN is reproted, and used to produce stereodefined (Z)-3,4-dihydronaphthalen-1(2H)-ones with a quaternary carbon center in generally good yields. [Display omitted] •A new Cu-catalyzed annulation-cyanotrifluoromethylation of 1,7-enynes is established.•The mechanism involves a CF3 radical addition-cyclization and radical coupling cascade.•This method provides a new entry for forming stereodefined (Z)-3,4-dihydronaphthalen-1(2H)-ones. A new three-component strategy for the copper-catalyzed annulation–cyanotrifluoromethylation of easily available 1,7-enynes with Togni’s reagent and TMSCN is developed. The reaction proceeds smoothly under mild conditions, providing a rapid and concise access to a wide range of stereodefined (Z)-3,4-dihydronaphthalen-1(2H)-ones with a quaternary carbon center in generally good yields. The protocol enjoys wide substrate scope regarding 1,7-enynes, high functional group tolerance and complete stereoselectivity.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152722