Investigations on the 1,2-Hydrogen Atom Transfer Reactivity of Alkoxyl Radicals under Visible-Light-Induced Reaction Conditions

被引：18
作者：
Liu, Dan [1 ]
Zhang, Jing [1 ]
Chen, Yiyun [1 ,2 ]
机构：
[1] Univ Chinese Acad Sci, Chinese Acad Sci, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem,State Key Lab Bioorgan &, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] Univ Chinese Acad Sci, Sch Chem & Mat Sci, Hangzhou Inst Adv Study, 1 Sub Lane Xiangshan, Hangzhou 310024, Peoples R China
来源：
SYNLETT | 2021年 / 32卷 / 04期
基金：
中国国家自然科学基金;
关键词：
alkoxyl radical; 1,2-HAT; C-H functionalization; photoredox catalysis; N-alkoxylphthalimide; N-alkoxylpyridinium salt; PHOTOREDOX CATALYSIS; RELAY CYCLIZATIONS; BETA-FRAGMENTATION; ALLYLATION; GENERATION; ALDITOLS;
D O I：
10.1055/a-1300-3453
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The alkoxyl radicals have demonstrated superior hydrogen atom transfer reactivity in organic synthesis due to the strong oxygen-hydrogen bond dissociation energy. However, only the intermolecular hydrogen atom transfer (HAT) and intramolecular 1,5-HAT have been widely studied and synthetically utilized for C(sp(3))-H functionalization. This Account summarizes our investigations on the unusual 1,2-HAT reactivity of alkoxyl radicals under visible-light-induced reaction conditions for the alpha-C-H functionalization. Various mechanistic investigations were discussed in this Account to address three key questions to validate the 1,2-HAT reactivity of alkoxyl radicals.
引用
收藏
页码：356 / 361
页数：6
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