BI-OAc-Accelerated C3-H Alkylation of Quinoxalin-2(1H)-ones under Visible-Light Irradiation

被引：128

作者：

He, Xiang-Kui ^{[1
,2
]}

Lu, Juan ^{[1
,2
]}

Zhang, Ai-Jun ^{[1
,2
]}

Zhang, Qing-Qing ^{[1
,2
]}

Xu, Guo-Yong ^{[1
,2
]}

Xuan, Jun ^{[1
,2
,3
]}

机构：

[1] Anhui Univ, Coll Chem & Chem Engn, Anhui Prov Key Lab Chem Inorgan Organ Hybrid Func, Hefei 230601, Anhui, Peoples R China

[2] Anhui Univ, Coll Chem & Chem Engn, Key Lab Funct Inorgan Mat Anhui Prov, Hefei 230601, Anhui, Peoples R China

[3] Anhui Univ, Key Lab Struct & Funct Regulat Hybrid Mat, Minist Educ, Hefei 230601, Anhui, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 15期

基金：

中国国家自然科学基金;

关键词：

C-H ALKYLATION; HANTZSCH ESTERS; DECARBOXYLATIVE ALKYNYLATION; TRANSFER HYDROGENATION; PHOTOREDOX; REAGENTS; 4-ALKYL-1,4-DIHYDROPYRIDINES; ACIDS; CHEMISTRY; CATALYSIS;

D O I：

10.1021/acs.orglett.0c02080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl radical precursors and acetoxybenziodoxole (BI-OAc) as an electron acceptor to undergo single-electron transfer with photoexcited R-DHPs. The benign conditions allow for good compatibility in the scope of both quinoxalin-2(1H)-ones and R-DHPs. The synthetic value of the protocol was also demonstrated by the successful functionalization of natural products and drug-based complex molecules

引用

页码：5984 / 5989

页数：6

共 50 条

[21] Catalyst-free visible-light-induced decarbonylative C-H alkylation of quinoxalin-2(1H)-ones
Shi, Xiaodi
Cao, Yunpeng
Liu, Yuxiu
Niu, Kaikai
Song, Hongjian
Zhang, Jingjing
Wang, Qingmin
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (05) : 1296 - 1300
[22] Visible-Light-Induced Divergent C-H Esterification/Alkylation of Quinoxalin-2(1H)-ones with Aldehydes under Mild Conditions
Hong, Yu
Xu, Jun
Chen, An
Du, Yating
Wang, Guangze
Shen, Jiabin
Zhang, Pengfei
ORGANIC LETTERS, 2025,
[23] Visible-Light-Induced Divergent C-H Esterification/Alkylation of Quinoxalin-2(1H)-ones with Aldehydes under Mild Conditions
Hong, Yu
Xu, Jun
Chen, An
Du, Yating
Wang, Guangze
Shen, Jiabin
Zhang, Pengfei
ORGANIC LETTERS, 2025, 27 (10) : 2526 - 2531
[24] Self-Catalyzed, Visible-Light-Induced Selective C3-H Aroylation of Quinoxalin-2(1H)-ones with Arylaldehydes by Air as an Oxidant
Liu, Wenhao
Liu, Xingyuan
Liu, Runjiao
Zhao, Hanqing
Xia, Zihao
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (10): : 7233 - 7242
[25] Ionic liquid-catalysed regioselective oxygenation of quinoxalin-2(1H)-ones under visible-light conditions
Badhani, Gaurav
Biramya, Valvi Mangesh
Adimurthy, Subbarayappa
NEW JOURNAL OF CHEMISTRY, 2023, 47 (47) : 21596 - 21599
[26] Direct C3-H carbamoylation of quinoxalin-2(1H)-ones with isocyanides enabled by selectfluor II under mild conditions
Li, Jing
Hu, Jie
Xiao, Yao
Yin, Kun
Dan, Wenyan
Fan, Suhua
Jin, Feng
Wu, Hai
Zhang, Ronghua
Li, Jian
TETRAHEDRON LETTERS, 2022, 88
[27] Covalent Organic Frameworks: A Sustainable Photocatalyst toward Visible-Light-Accelerated C3 Arylation and Alkylation of Quinoxalin-2(1H)-ones
Tian, Miao
Liu, Shuyang
Bu, Xiubin
Yu, Jipan
Yang, Xiaobo
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (02) : 369 - 373
[28] Iron-catalyzed methylation of quinoxalin-2(1H)-ones with dimethyl sulfoxide under visible light irradiation
He, Hong
Zhang, Zhongyi
Zhang, Yicheng
Zhou, Chao
Liu, Jie
Wang, Lei
MOLECULAR CATALYSIS, 2024, 558
[29] The visible-light-triggered regioselective alkylation of quinoxalin-2(1H)-ones via decarboxylation coupling
Zhang, Hongdou
Xu, Jun
Zhou, Min
Zhao, Jianming
Zhang, Pengfei
Li, Wanmei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (48) : 10201 - 10208
[30] Visible-Light-Induced Direct C-H Amination of Quinoxalin-2(1H)-ones
Liu, Yanpeng
Pei, Congcong
Chen, Xiaoyu
Zhang, Jianye
Li, Jingya
Zou, Dapeng
Wu, Yangjie
Wu, Yusheng
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (05) : 709 - 714

← 1 2 3 4 5 →