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(sp3)—C(sp3)键
收稿日期: 2022-09-19
修回日期: 2022-10-19
网络出版日期: 2022-11-15
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
Received date: 2022-09-19
Revised date: 2022-10-19
Online published: 2022-11-15
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
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.
孙丽 , 宋国欣 , 韩家乐 , 李继玉 , 赵月 , 杨璐华 , 张峰 , 赵坤 , 毛比明 . 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(sp3)—C(sp3)键[J]. 有机化学, 2023 , 43(4) : 1574 -1583 . DOI: 10.6023/cjoc202209024
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.
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