Selectfluor-Mediated Stereoselective [1 + 1 + 4 + 4] Dimerization of Styrylnaphthols
Hui Yang1, Huai-Ri Sun1, Rui-Di Xue1
1Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, National Demonstration Center for Experimental Chemistry Education , Northwest University , Xi'an 710127 , P.R. China.
Abstract:
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.
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