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; Yong-Chun Luo

doi:10.1039/d3cc02988c

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

Chem Commun (Camb). 2023 Sep 21;59(76):11385-11388. doi: 10.1039/d3cc02988c.

Authors

Yi-Lin Wang¹, Xin-Xin Lei¹, Xin-Chen Jin¹, Xin-Yu Zhang¹, Peng-Fei Xu^{1

2}, Yong-Chun Luo^{1

2}

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, College of Veterinary Medicine, Lanzhou University, Lanzhou, 730000, P. R. China. luoych@lzu.edu.cn.
² State Key Laboratory of Veterinary Etiological Biology, Lanzhou Veterinary Research Institute, Chinese Academy of Agricultural Sciences, Lanzhou 730000, P. R. China.

PMID: 37667576
DOI: 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.