通过光氧化还原 1,2-氢原子转移实现 N-(苯甲氧基)邻苯二甲酰亚胺与氰基吡啶的苄位 C-H 杂芳基化反应。
Benzylic C-H heteroarylation of N-(benzyloxy)phthalimides with cyanopyridines enabled by photoredox 1,2-hydrogen atom transfer.
机构信息
State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, China.
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China.
出版信息
Chem Commun (Camb). 2020 Jul 31;56(61):8671-8674. doi: 10.1039/d0cc03619f.
A visible light initiated α-C(sp3)-H arylation of N-(benzyloxy)phthalimides with cyanopyridines for the construction of highly valuable pyridinyl-containing diarylmethanols, including bioactive motif-based analogues, is reported. This method enables arylation of the C(sp3)-H bonds adjacent to an oxygen atom through alkoxy radical formation by O-N bond cleavage, 1,2-hydrogen atom transfer (HAT), arylation and C-CN bond cleavage cascades, and offers a means to exploit 1,2-HAT modes to incorporate functional groups for constructing functionalized alcohols.
本文报道了可见光引发的 N-(苯氧基亚甲基)邻苯二甲酰亚胺与氰基吡啶的 α-C(sp3)-H 芳基化反应，用于构建高价值的含吡啶基二芳基甲醇，包括基于生物活性基序的类似物。该方法通过 O-N 键断裂、1,2-氢原子转移 (HAT)、芳基化和 C-CN 键断裂级联反应，实现了与氧原子相邻的 C(sp3)-H 键的芳基化，为利用 1,2-HAT 模式引入官能团构建功能化醇提供了一种手段。
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