Morita-Baylis-Hillman加合物和N-羟基邻苯二甲酰亚胺的电化学烯丙基烷基化形成C(sp^(3))-C(sp^(3))键  

Electrochemical Allylic Alkylation of Morita-Baylis-Hillman Adducts and N-Hydroxyphthalimide Esters towards C(sp^(3))-C(sp^(3))Bond Formation

作　　者：孙丽 宋国欣 韩家乐 李继玉 赵月 杨璐华 张峰 赵坤 毛比明 Sun Li;Song Guoxin;Han Jiale;Li Jiyu;Zhao Yue;Yang Luhua;Zhang Feng;Zhao Kun;Mao Biming(School of Parmacy and Pharmaceutical Science&Institute of Materia Medica,Shandong First Medical University&Shandong Academy of Medical Sciences,Jinan 250117;Key Laboratory of Chemical Biology(Ministry of Education),School of Pharmaceutical Sciences,Shandong University,Jinan 250012)

机构地区：[1]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 [2]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

出　　处：《有机化学》2023年第4期1574-1583,共10页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.22101156,22101154);山东省自然科学基金(Nos.ZR2021QB032,ZR2021QB038);泰山学者工程专项经费资助项目。

摘　　要：报道了一种无外加氧化还原剂、电还原方法,使Morita-Baylis-Hillman (MBH)加合物实现烯丙基烷基化.这种转变的一个关键特征是,既不需要外部化学还原剂也不需要金属催化剂. N-烷酰氧基邻苯二甲酰亚胺(NHP)酯通过电子还原产生烷基自由基,在烷基化过程中以高立体选择性和区域选择性展示出对烯烃取代的广泛官能团耐受性.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.

关 键 词：烯丙基烷基化 Morita-Baylis-Hillman(MBH)加合物 电化学还原路径 

分 类 号：O621.25[理学—有机化学]