通过伴随的1,2-芳基迁移实现可见光促进的未活化烯烃与二甲基亚砜的氧化烷基化反应
Visible-Light-Enabled Oxidative Alkylation of Unactivated Alkenes with Dimethyl Sulfoxide through Concomitant 1,2-Aryl Migration.
作者信息
Lu Maojian, Qin Honggui, Lin Zhaowei, Huang Mingqiang, Weng Wen, Cai Shunyou
机构信息
Key Laboratory of Modern Analytical Science and Separation Technology of Fujian Province, School of Chemistry, Chemical Engineering, and Environment , Minnan Normal University , Zhangzhou 363000 , China.
Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology , Peking University, Shenzhen Graduate School , Shenzhen 518055 , China.
出版信息
Org Lett. 2018 Dec 7;20(23):7611-7615. doi: 10.1021/acs.orglett.8b03340. Epub 2018 Nov 28.
Metal-free oxidative radical 1,2-alkylarylation of unactivated alkenes with the α-C(sp)-H bond of dimethyl sulfoxide has been developed. This study realizes a new, conceptually novel technology for convenient construction of a variety of α-aryl-γ-methylsulfinyl ketones in good-to-excellent yields with the synergistic interactions of visible light irradiation, organic fluorophores 4CzIPN, and hypervalent iodine(III) reagent under transition-metal free conditions. A remarkable kinetic isotope effect was observed, which helped provide insight into the reaction's mechanistic course.
已开发出在无金属条件下，未活化烯烃与二甲基亚砜的α-C(sp)-H键进行无金属氧化自由基1,2-烷基芳基化反应。该研究实现了一种全新的、概念新颖的技术，即在可见光照射、有机荧光团4CzIPN和高价碘(III)试剂的协同作用下，在无过渡金属条件下以良好至优异的产率方便地构建各种α-芳基-γ-甲基亚磺酰基酮。观察到显著的动力学同位素效应，这有助于深入了解反应的机理过程。
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