Electrochemical remote C(sp3)-H thiocyanation

被引：5
|
作者：
Pang, Xinyu [1 ]
He, Hui [2 ,3 ]
Meng, Xiangrui [1 ]
Zhang, Linbao [1 ]
Ni, Shaofei [2 ,3 ]
Li, Ming [1 ]
Guo, Weisi [1 ]
机构：
[1] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, 53 Zhengzhou Rd, Qingdao, Peoples R China
[2] Shantou Univ, Dept Chem, Shantou 515063, Guangdong, Peoples R China
[3] Shantou Univ, Key Lab Preparat & Applicat Ordered Struct Mat Gua, Shantou 515063, Guangdong, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 08期
关键词：
AMINATION; RADICALS; METAL; GENERATION; IODINE;
D O I：
10.1039/d4qo00032c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The amidyl radical-mediated 1,5-HAT is a powerful strategy to realize distal C(sp(3))-H functionalization. Recently, organic electrosynthesis has provided a sustainable method for the generation of nitrogen-centered radicals. However, current approaches based on electrochemically promoted 1,5-HAT are limited to the Hofmann-Loffler-Freytag (HLF) reaction. We report herein a solution to this challenge by trapping the generated carbocation with TMSNCS to achieve the distal C(sp(3))-H thiocyanation. Control experiments and DFT calculations support the radical-polar crossover mechanism. The reaction has a broad substrate scope, including primary, secondary, and tertiary substrates and bioactive molecules.
引用
收藏
页码：2283 / 2288
页数：6
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