Combining Gold and Photoredox Catalysis: Visible Light-Mediated Oxy- and Aminoarylation of Alkenes

被引:429
|
作者
Sahoo, Basudev [1 ]
Hopkinson, Matthew N. [1 ]
Glorius, Frank [1 ]
机构
[1] Univ Munster, NRW Grad Sch Chem, Inst Organ Chem, D-48149 Munster, Germany
基金
欧洲研究理事会;
关键词
ARYL DIAZONIUM SALTS; C-H ARYLATION; CROSS-COUPLING REACTIONS; UNACTIVATED ALKENES; DUAL CATALYSIS; METAL-FREE; PALLADIUM; ALDEHYDES; PHOTOCATALYSIS; OXYARYLATION;
D O I
10.1021/ja400311h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A room-temperature intramolecular oxy- and aminoarylation of alkenes with aryldiazonium salts has been developed using a novel gold and photoredox dual-catalytic system. The compatibility of these two catalytic modes has been established for the first time and demonstrates the potential of this system as a method to expand the scope of nucleophilic addition reactions to carbon-carbon multiple bonds.
引用
收藏
页码:5505 / 5508
页数:4
相关论文
共 50 条
  • [1] Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes
    Li, Haoyu
    Shan, Cuicui
    Tung, Chen-Ho
    Xu, Zhenghu
    CHEMICAL SCIENCE, 2017, 8 (04) : 2610 - 2615
  • [2] Enchained by visible light-mediated photoredox catalysis
    Kaerkaes, Markus D.
    Matsuura, Bryan S.
    Stephenson, Corey R. J.
    SCIENCE, 2015, 349 (6254) : 1285 - 1286
  • [3] Mechanism of Visible Light-Mediated Alkene Aminoarylation with Arylsulfonylacetamides
    Allen, Anthony R.
    Poon, Jia-Fei
    McAtee, Rory C.
    Watson, Nicholas B.
    Pratt, Derek A.
    Stephenson, Corey R. J.
    ACS CATALYSIS, 2022, 12 (14): : 8511 - 8526
  • [4] Synthesis of symmetric anhydrides using visible light-mediated photoredox catalysis
    Konieczynska, Marlena D.
    Dai, Chunhui
    Stephenson, Corey R. J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (23) : 4509 - 4511
  • [5] Trifluoromethylation of Alkenes by Visible Light Photoredox Catalysis
    Iqbal, Naeem
    Choi, Sungkyu
    Kim, Eunjin
    Cho, Eun Jin
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (24): : 11383 - 11387
  • [6] Photoredox-Catalyzed Oxy-/Aminofluoroalkylative Cyclization of Alkenes
    Liao, Jianhua
    Ouyang, Lu
    Lai, Yinlong
    Luo, Renshi
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (08): : 5590 - 5597
  • [7] Hydrosulfonylation of Unactivated Alkenes by Visible Light Photoredox Catalysis
    Wang, Juan-Juan
    Yu, Wei
    ORGANIC LETTERS, 2019, 21 (22) : 9236 - 9240
  • [8] Recent Applications of [Cu(dap)2]Cl in Visible Light-Mediated Photoredox Catalysis
    Olding, Angus
    Nicholls, Thomas P.
    Bissember, Alex C.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2018, 71 (07) : 547 - 548
  • [9] Visible Light-Mediated Coupling of α-Bromochalcones with Alkenes
    Paria, Suva
    Kais, Viktor
    Reiser, Oliver
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (13) : 2853 - 2858
  • [10] Mechanism of the Visible Light-Mediated Gold-Catalyzed Oxyarylation Reaction of Alkenes
    Zhang, Qi
    Zhang, Zhen-Qi
    Fu, Yao
    Yu, Hai-Zhu
    ACS CATALYSIS, 2016, 6 (02): : 798 - 808