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

页码：356 / 361

页数：6

共 50 条

[31] Reactivity and Mechanistic Insight into Visible-Light-Induced Aerobic Cross-Dehydrogenative Coupling Reaction by Organophotocatalysts
Liu, Qiang
Li, Ya-Nan
Zhang, Hui-Hui
Chen, Bin
Tung, Chen-Ho
Wu, Li-Zhu
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (02) : 620 - 627
[32] Visible-Light-Induced Photocatalytic Oxidative Decarboxylation of Cinnamic Acids to 1,2-Diketones
Chand, Shiv
Pandey, Anand Kumar
Singh, Rahul
Singh, Krishna Nand
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (09): : 6486 - 6493
[33] Visible-Light-Induced Hydrogen Atom Transfer En Route to Exocylic Alkenylation of Cyclic Ethers Enabled by Electron Donor-Acceptor Complex
Mandal, Tanumoy
Das, Sanju
Maji, Rohan
De Sarkar, Suman
ORGANIC LETTERS, 2023, 25 (42) : 7727 - 7732
[34] Visible-Light-Induced Heptacene Generation under Ambient Conditions: Utilization of Single-crystal Interior as an Isolated Reaction Site
Hayashi, Hironobu
Hieda, Nao
Yamauchi, Mitsuaki
Chan, Yee Seng
Aratani, Naoki
Masuo, Sadahiro
Yamada, Hiroko
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (66) : 15079 - 15083
[35] Tuning Reactivity and Selectivity in Hydrogen Atom Transfer from Aliphatic C-H Bonds to Alkoxyl Radicals: Role of Structural and Medium Effects
Salamone, Michela
Bietti, Massimo
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (11) : 2895 - 2903
[36] Cascade cyclization for the synthesis of indolo[2,1-α]isoquinoline derivatives via visible-light-induced halogen-atom-transfer (XAT) and hydrogen-atom-transfer (HAT)
Ma, Na
Guo, Lin
Shen, Zheng-Jia
Qi, Dan
Yang, Chao
Xia, Wujiong
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (08) : 1731 - 1737
[37] Visible-light-induced chemoselective reductive decarboxylative alkynylation under biomolecule-compatible conditions
Yang, Jie
Zhang, Jing
Qi, Li
Hu, Chenchen
Chen, Yiyun
CHEMICAL COMMUNICATIONS, 2015, 51 (25) : 5275 - 5278
[38] Reaction Pathways of Alkoxyl Radicals. The Role of Solvent Effects on C-C Bond Fragmentation and Hydrogen Atom Transfer Reactions
Salamone, Michela
Bietti, Massimo
SYNLETT, 2014, 25 (13) : 1803 - 1816
[39] Visible light-induced hydrogen atom transfer trifluoromethylthiolation of aldehydes with bismuth catalyst
Dong, Jun
Tang, Zhuang
Zou, Luqian
Zhou, Yongyun
Chen, Jingchao
CHEMICAL COMMUNICATIONS, 2024, 60 (06) : 742 - 745
[40] Visible-Light-Induced Carbopyridylation of Maleimides with Pyridine Salts Under Catalyst-Free Conditions
Ma, Zijia
Wang, He
Li, Chunbo
Liu, Ningning
Wang, Yujia
Sun, Jing
Wang, Xin
Sun, Ran
Li, Lei
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 14 (03)

← 1 2 3 4 5 →