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

[1] Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer
Yang, Zhaoliang
Niu, Yunhong
He, Xiaoqian
Chen, Suo
Liu, Shanshan
Li, Zhengyu
Chen, Xiang
Zhang, Yunxiao
Lan, Yu
Shen, Xiao
NATURE COMMUNICATIONS, 2021, 12 (01)
[2] Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer
Zhaoliang Yang
Yunhong Niu
Xiaoqian He
Suo Chen
Shanshan Liu
Zhengyu Li
Xiang Chen
Yunxiao Zhang
Yu Lan
Xiao Shen
Nature Communications, 12
[3] Visible-light-driven net-1,2-hydrogen atom transfer of amidyl radicals to access β-amido ketone derivatives
Jiang, Yonggang
Li, Hui
Tang, Haoqin
Zhang, Qingyue
Yang, Haitao
Pan, Yu
Zou, Chenggang
Zhang, Hongbin
Walsh, Patrick J.
Yang, Xiaodong
CHEMICAL SCIENCE, 2025, 16 (02) : 962 - 969
[4] Net-1,2-Hydrogen Atom Transfer of Amidyl Radicals: Toward the Synthesis of 1,2-Diamine Derivatives
Jiang, Yonggang
Liu, Dongxiang
Rotella, Madeline E.
Deng, Guogang
Liu, Zhengfen
Chen, Wen
Zhang, Hongbin
Kozlowski, Marisa C.
Walsh, Patrick J.
Yang, Xiaodong
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (29) : 16045 - 16057
[5] Visible-light-induced dehydrogenation of dihydroquinolinones via the combination of energy transfer and hydrogen atom transfers
Feng, Jin
Tang, Hanguang
Guo, Hao
Ding, Aishun
ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (04): : 1183 - 1188
[6] Visible-Light-Induced Alkoxyl Radicals Enable α-C(sp3)-H Bond Allylation
Zhang, Jing
Liu, Dan
Liu, Song
Ge, Yuanyuan
Lan, Yu
Chen, Yiyun
ISCIENCE, 2020, 23 (01)
[7] Electrochemical 1,2-hydrogen atom transfer functionalizations of N-(benzyloxy)phthalimides
Fu, Xin
Ran, Tingting
Liu, Jie
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (23): : 6760 - 6767
[8] Visible-Light-Induced Three-Component 1,2-Alkylpyridylation of Alkenes via a Halogen-Atom Transfer Process
Yu, Weijie
Wang, Hongyu
Zhao, Kuang
Li, Wendong
Wang, Tao
Fu, Junkai
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (03): : 1703 - 1708
[9] Visible-Light-Induced Dearomatization via [2+2] Cycloaddition or 1,5-Hydrogen Atom Transfer: Divergent Reaction Pathways of Transient Diradicals
Zhu, Min
Zhang, Xiao
Zheng, Chao
You, Shu-Li
ACS CATALYSIS, 2020, 10 (21) : 12618 - 12626
[10] Visible-light-induced transition-metal-free defluorosilylation of α-trifluoromethylalkenes via hydrogen atom transfer of silanes
Xu, Wengang
Xia, Congjian
Shao, Qi
Zhang, Qiao
Liu, Mingrui
Zhang, Hongwei
Wu, Mingbo
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (18): : 4949 - 4954

← 1 2 3 4 5 →