Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1574-1583.DOI: 10.6023/cjoc202209024 Previous Articles     Next Articles



孙丽a, 宋国欣a, 韩家乐a, 李继玉a, 赵月a, 杨璐华a, 张峰a, 赵坤b, 毛比明a,*()   

  1. a 山东第一医科大学(山东省医学科学院)药学与制药科学学院(药物研究所) 济南 250117
    b 山东大学药学院 天然产物化学生物学教育部重点实验室 济南 250012
  • 收稿日期:2022-09-19 修回日期:2022-10-19 发布日期:2022-11-15
  • 通讯作者: 毛比明
  • 基金资助:
    国家自然科学基金(22101156); 国家自然科学基金(22101154); 山东省自然科学基金(ZR2021QB032); 山东省自然科学基金(ZR2021QB038); 泰山学者工程专项经费资助项目

Electrochemical Allylic Alkylation of Morita-Baylis-Hillman Adducts and N-Hydroxyphthalimide Esters towards C(sp3)—C(sp3) Bond Formation

Li Suna, Guoxin Songa, Jiale Hana, Jiyu Lia, Yue Zhaoa, Luhua Yanga, Feng Zhanga, Kun Zhaob, Biming Maoa()   

  1. a School of Parmacy and Pharmaceutical Science & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117
    b Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, Jinan 250012
  • Received:2022-09-19 Revised:2022-10-19 Published:2022-11-15
  • Contact: Biming Mao
  • Supported by:
    National Natural Science Foundation of China(22101156); National Natural Science Foundation of China(22101154); Natural Science Foundation of Shandong Province(ZR2021QB032); Natural Science Foundation of Shandong Province(ZR2021QB038); Taishan Scholar Youth Program of Shandong Province

A redox-free, electroreductive approach to achieve allylic alkylation by employing Morita-Baylis-Hillman (MBH) adducts is reported. A critical feature of this transformation is that neither external chemical oxidants nor metal catalysts are required. Alkyl radical produced by electron reduction with N-hydroxyphthalimide (NHP) esters, displaying broad tolerance of functional groups and alkene substitution patterns in high stereoselectivity and regioselectivity.

Key words: allylic alkylation, Morita-Baylis-Hillman (MBH) adducts, electroreductive approach