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
收藏
页码：5984 / 5989
页数：6
相关论文
共 50 条
  • [1] Photoinduced Decarboxylative C3-H Alkylation of Quinoxalin-2(1H)-ones
    Bisoyi, Akash
    Tripathy, Alisha Rani
    Yedase, Girish Suresh
    Sinu, P. Shifana
    Choudhury, Udita
    Yatham, Veera Reddy
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (04): : 2631 - 2641
  • [2] Visible-Light-Mediated C3-H Acetalation of Quinoxalin-2(1H)-ones
    Zhang Mengqi
    Nan Guangming
    Zhao Xiaohui
    Wei Wei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (12) : 4315 - 4322
  • [3] Visible-light induced decarboxylative alkylation of quinoxalin-2(1H)-ones at the C3-position
    Xue, Wenxuan
    Su, Yingpeng
    Wang, Ke-Hu
    Zhang, Rong
    Feng, Yawei
    Cao, Lindan
    Huang, Dangfeng
    Hu, Yulai
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (27) : 6654 - 6661
  • [4] Recent Advances in Visible-Light-Enabled C3-H Fluoroalkylation of Quinoxalin-2(1H)-ones
    Ma, Dong
    Wu, Xinfen
    Xiao, Tiebo
    CHEMISTRYSELECT, 2025, 10 (12):
  • [5] Visible light-promoted C3-H alkoxycarbonylation of quinoxalin-2(1H)-ones or coumarins with alkyloxalyl chlorides
    Lin, Yanchun
    Zhou, Xi
    Zheng, Yixuan
    Chen, Bingran
    Liu, Yang
    Zhang, Yi
    Yan, Qiongjiao
    Wang, Wei
    Chen, Fener
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (43) : 8591 - 8595
  • [6] Visible-light-induced aerobic C3-H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols
    Xu, Xiaobo
    Xia, Chengcai
    Li, Xiaojun
    Sun, Jian
    Hao, Liqiang
    RSC ADVANCES, 2020, 10 (04) : 2016 - 2026
  • [7] Photoredox Catalyst Free, Visible Light-Promoted C3-H Acylation of Quinoxalin-2(1H)-ones in Water
    Lu, Juan
    He, Xiang-Kui
    Cheng, Xiao
    Zhang, Ai-Jun
    Xu, Guo-Yong
    Xuan, Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (11) : 2178 - 2182
  • [8] C-H benzylation of quinoxalin-2(1H)-ones via visible-light riboflavin photocatalysis
    Yan, Qiuli
    Cui, Wenwen
    Li, Junxin
    Xu, Guiyun
    Song, Xiuyan
    Lv, Jian
    Yang, Daoshan
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (10): : 2653 - 2658
  • [9] Visible-light induced C3-H trifluoromethylation of quinoxalin-2(1H)-ones with CF3SO2Cl under external photocatalyst-free conditions
    Mi, Xia
    Cui, Beibei
    Zhang, Jingyu
    Pi, Chao
    Cui, Xiuling
    TETRAHEDRON LETTERS, 2022, 93
  • [10] Iron-Catalyzed Direct C3-H Trifluoromethylthiolation of Quinoxalin-2(1H)-ones
    Chen, Xiaoyu
    Geng, Yang
    Zhu, Yu
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (02) : 214 - 219
12345