Visible light-induced aerobic C-N bond activation: a photocatalytic strategy for the preparation of 2-arylpyridines and 2-arylquinolines

被引:15
作者
Hu, Bei [1 ]
Li, Yuyuan [2 ,3 ]
Dong, Wuheng [1 ]
Xie, Xiaomin [1 ]
Wan, Jun [2 ,3 ]
Zhang, Zhaoguo [1 ,4 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
[2] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, 53 Zhengzhou Rd, Qingdao 266042, Peoples R China
[3] Qingdao Univ Sci & Technol, Coll Environm & Safety Engn, 53 Zhengzhou Rd, Qingdao 266042, Peoples R China
[4] Chinese Acad Sci, Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源
RSC ADVANCES | 2016年 / 6卷 / 54期
基金
中国国家自然科学基金;
关键词
METAL-CATALYZED REACTIONS; CROSS-COUPLING REACTIONS; AMINO CARBONYL-COMPOUNDS; PHOTOREDOX CATALYSIS; MOLECULAR-OXYGEN; TERTIARY-AMINES; H ACTIVATION; VINYL AZIDES; OXIDATION; QUINOLINES;
D O I
10.1039/c6ra07962h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient method for accessing arylpyridines and arylquinolines via visible light-induced aerobic C-N bond activation is described. The applicability of different kinds of simple ketones, easily available amines, and the use of air as the sole oxidant make this transformation very attractive.
引用
收藏
页码:48315 / 48318
页数:4
相关论文
共 63 条
  • [1] Dicarbonyliridium(I) complexes of pyridine ester ligands and their reactivity towards various electrophiles
    Bora, Dimpi
    Deb, Biswajit
    Fuller, Amy L.
    Slawin, Alexandra M. Z.
    Woollins, J. Derek
    Dutta, Dipak Kumar
    [J]. INORGANICA CHIMICA ACTA, 2010, 363 (07) : 1539 - 1546
  • [2] The total synthesis of streptonigrin and related antitumor antibiotic natural products
    Bringmann, G
    Reichert, Y
    Kane, VV
    [J]. TETRAHEDRON, 2004, 60 (16) : 3539 - 3574
  • [3] 7-methoxyfuro[2,3-c]pyridine-4-carboxamides as PDE4 inhibitors:: A potential treatment for asthma
    Buckley, GM
    Cooper, N
    Davenport, RJ
    Dyke, HJ
    Galleway, FP
    Gowers, L
    Haughan, AF
    Kendall, HJ
    Lowe, C
    Montana, JG
    Oxford, J
    Peake, JC
    Picken, CL
    Richard, MD
    Sabin, V
    Sharpe, A
    Warneck, JBH
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (03) : 509 - 512
  • [4] Metal-free aerobic oxidative C-N bond cleavage of tertiary amines for the synthesis of N-heterocycles with high atom efficiency
    Chen, Xiuling
    Chen, Tieqiao
    Zhou, Yongbo
    Han, Daoqing
    Han, Li-Biao
    Yin, Shuang-Feng
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (23) : 3802 - 3807
  • [5] Synthesis of dihydropyridines and pyridines from Imines and alkynes via C-H activation
    Colby, Denise A.
    Bergman, Robert G.
    Ellman, Jonathan A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) : 3645 - 3651
  • [6] Visible-light-induced photocatalytic oxytrifluoromethylation of N-allylamides for the synthesis of CF3-containing oxazolines and benzoxazines
    Deng, Qiao-Hui
    Chen, Jia-Rong
    Wei, Qiang
    Zhao, Quan-Qing
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (17) : 3537 - 3540
  • [7] Ring-closing metathesis for the synthesis of heteroaromatics: evaluating routes to pyridines and pyridazines
    Donohoe, Timothy J.
    Bower, John F.
    Basutto, Jose A.
    Fishlock, Lisa P.
    Procopiou, Panayiotis A.
    Callens, Cedric K. A.
    [J]. TETRAHEDRON, 2009, 65 (44) : 8969 - 8980
  • [8] Synthesis and Biological Evaluation of Pyridine-Containing Lipoxin A4 Analogues
    Duffy, Colm D.
    Maderna, Paola
    McCarthy, Ciara
    Loscher, Christine E.
    Godson, Catherine
    Guiry, Patrick J.
    [J]. CHEMMEDCHEM, 2010, 5 (04) : 517 - 522
  • [9] Enantioselective Conjugate Additions of α-Amino Radicals via Cooperative Photoredox and Lewis Acid Catalysis
    Espelt, Laura Ruiz
    McPherson, Iain S.
    Wiensch, Eric M.
    Yoon, Tehshik P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (07) : 2452 - 2455
  • [10] Combining Rhodium and Photoredox Catalysis for C-H Functionalizations of Arenes: Oxidative Heck Reactions with Visible Light
    Fabry, David C.
    Zoller, Jochen
    Raja, Sadiya
    Rueping, Magnus
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (38) : 10228 - 10231