Sc(OTf)3 catalyzed intramolecular single-electron transfer of 2-alkyl-1,4-benzoquinones: synthesis of 6-chromanols from donor–acceptor cyclopropanes†

Yi-Lin Wang,‡ Xin-Xin Lei,‡ Xin-Chen Jin,  Xin-Yu Zhang,  Peng-Fei Xu*  and  Yong-Chun Luo*

https://doi.org/10.1039/D3CC02988C

Abstract:A Sc(OTf)3 catalyzed intramolecular cyclization reaction of 2-alkyl-1,4-benzoquinone derived from D–A cyclopropane was discovered. This reaction involves single-electron transfer, proton-transfer, an aromatization driven spin center shift, and radical coupling processes, and offers an efficient method for the synthesis of 6-chromanols from D–A cyclopropanes.