Selectfluor-Mediated Stereoselective [1 + 1 + 4 + 4] Dimerization of Styrylnaphthols

Stereoselective [1 + 1 + 4 + 4] dimerization of 1-styrylnaphthols has been developed by using Selectfluor as the oxidant for the first time. The reaction was compatible with various functional groups, giving a class of ethanodinaphtho­[b,f]­[1,5]­dioxocines with novel 3D skeletons. DFT calculations...

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Bibliographic Details
Published in:Organic letters 2019-12, Vol.21 (24), p.9829-9835
Main Authors: Yang, Hui, Sun, Huai-Ri, Xue, Rui-Di, Wu, Zi-Bo, Gou, Bo-Bo, Lei, Yibo, Chen, Jie, Zhou, Ling
Format: Article
Language:English
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Summary:Stereoselective [1 + 1 + 4 + 4] dimerization of 1-styrylnaphthols has been developed by using Selectfluor as the oxidant for the first time. The reaction was compatible with various functional groups, giving a class of ethanodinaphtho­[b,f]­[1,5]­dioxocines with novel 3D skeletons. DFT calculations indicate that this method merges an intriguing stereoselective intermolecular 1 + 1 radical coupling to construct a bridged C–C bond and then an intramolecular [4 + 4] formal cycloaddition of the in situ generated o-quinone methide intermediate.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03587