Visible-Light-Promoted C2 Selective Arylation of Quinoline and Pyridine N-Oxides with Diaryliodonium Tetrafluoroborate

被引:37
|
作者
Li, Dazhi [1 ]
Liang, Ce [2 ]
Jiang, Zaixing [2 ]
Zhang, Junzheng [2 ]
Zhuo, Wang-Tao [2 ]
Zou, Fan-Yue [2 ]
Wang, Wan-Peng [2 ]
Gao, Guo-Lin [2 ]
Song, Jinzhu [1 ]
机构
[1] Harbin Inst Technol, Sch Life Sci & Technol, Harbin 150001, Heilongjiang, Peoples R China
[2] Harbin Inst Technol, Sch Chem & Chem Engn, MIIT Key Lab Crit Mat Technol New Energy Convers, Harbin 150001, Heilongjiang, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 04期
关键词
CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; H ARYLATION; PALLADIUM COMPLEXES; ARYL; HETEROARYL; SALTS; HETEROCYCLES; PHOSPHINE; REDUCTION;
D O I
10.1021/acs.joc.9b02933
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A protocol of visible-light-promoted C2 selective arylation of quinoline and pyridine N-oxides, with diaryliodonium tetrafluoroborate as an arylation reagent, using eosin Y as a photocatalyst for the construction of N-heterobiaryls was presented. This methodology provided an efficient way for the synthesis of 2-aryl-substituted quinoline and pyridine N-oxides. This strategy has the following advantages: specific regioselectivity, simple operation, good functional group tolerance, and high to moderate yields under mild conditions.
引用
收藏
页码:2733 / 2742
页数:10
相关论文
共 50 条
  • [31] Visible-Light-Induced C2 Alkylation of Heterocyclic N-Oxides with N-Hydroxyphthalimide Esters under Metal-Free Conditions
    Qin, Pi-Tao
    Sun, Jing
    Wang, Fei
    Wang, Jing-Yun
    Wang, He
    Zhou, Ming-Dong
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (21) : 4707 - 4715
  • [32] Visible light-mediated direct C8-H arylation of quinolines and C2-H arylation of quinoline-N-oxides and pyridines under organic photocatalysis
    Banu, Saira
    Singh, Kuldeep
    Yadav, Prem P.
    NEW JOURNAL OF CHEMISTRY, 2024, 48 (04) : 1481 - 1488
  • [33] Rh(III)-Catalyzed Selective C8-H Acylmethylation of Quinoline N-Oxides
    You, Chang
    Pi, Chao
    Wu, Yangjie
    Cui, Xiuling
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (21) : 4068 - 4072
  • [34] C2-Arylation of Substituted Pyridine N-oxides with Heteroaryl Carboxylic Acids by Palladium-Catalyzed Decarboxylative Coupling
    Suresh, Rajendran
    Muthusubramanian, Shanmugam
    Kumaran, Rajendran Senthil
    Manickam, Govindaswamy
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (05) : 604 - 608
  • [35] Synthesis of 2-substituted pyridines via a regiospecific alkylation, alkynylation, and arylation of pyridine N-oxides
    Andersson, Hans
    Almqvist, Fredrik
    Olsson, Roger
    ORGANIC LETTERS, 2007, 9 (07) : 1335 - 1337
  • [36] Visible-Light-Promoted Activation of Unactivated C(sp3)-H Bonds and Their Selective Trifluoromethylthiolation
    Mukherjee, Satobhisha
    Maji, Biplab
    Tlahuext-Aca, Adrian
    Glorius, Frank
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (50) : 16200 - 16203
  • [37] Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinoline N-oxides
    Mandal, Susanta
    Bhuyan, Samuzal
    Jana, Saibal
    Hossain, Jagir
    Chhetri, Karan
    Roy, Biswajit Gopal
    GREEN CHEMISTRY, 2021, 23 (14) : 5049 - 5055
  • [38] A visible-light-promoted aerobic C-H/C-N cleavage cascade to isoxazolidine skeletons
    Xie, Jin
    Xue, Qicai
    Jin, Hongming
    Li, Huamin
    Cheng, Yixiang
    Zhu, Chengjian
    CHEMICAL SCIENCE, 2013, 4 (03) : 1281 - 1286
  • [39] Visible-Light-Mediated C-2 Functionalization and Deoxygenative Strategies in Heterocyclic N-Oxides
    Singh, Jitender
    Patel, Roshan, I
    Sharma, Anuj
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (14) : 2289 - 2306
  • [40] Regioselective Arylation of Quinoline N-Oxides (C8), Indolines (C7) and N-tert-Butylbenzamide with Arylboronic Acids
    Gupta, Shiv Shankar
    Kumar, Rakesh
    Sharma, Upendra
    ACS OMEGA, 2020, 5 (01): : 904 - 913