Li Xue, Liao Lin-Fen, Ding Li-Yao, Chen Chun-Hua, Liang Cui, Mo Dong-Liang
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, China.
Key Laboratory of Chemistry and Engineering of Forest Products, State Ethnic Affairs Commision, Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning 530008, China.
Org Lett. 2024 Apr 19;26(15):3060-3064. doi: 10.1021/acs.orglett.4c00693. Epub 2024 Mar 29.
We described an iron(III) and BF·OEt-promoted oxygen transfer reaction of -aryl-α,β-unsaturated nitrones to prepare various ,-difluoroboron β-ketoiminates in good yields ranging from 24% to 87%. Control experiments revealed that the enaminone was the vital intermediate for the formation of ,-difluoroboron β-ketoiminates, and iron(III) combined with BF·OEt played as cocatalyst to promote the oxygen transfer reaction through intramolecular cyclization and N-O bond cleavage. More importantly, an estrone-derived ,-difluoroboron β-ketoiminate was easily prepared in 40% yield from estrone in four steps.
我们描述了一种铁（III）和BF·OEt促进的芳基-α，β-不饱和硝酮的氧转移反应，以良好的产率（24%至87%）制备各种β，β-二氟硼β-酮亚胺。对照实验表明，烯胺酮是形成β，β-二氟硼β-酮亚胺的关键中间体，铁（III）与BF·OEt结合作为共催化剂，通过分子内环化和N-O键断裂促进氧转移反应。更重要的是，从雌酮出发，通过四步反应可以轻松制备出产率为40%的雌酮衍生的β，β-二氟硼β-酮亚胺。
