Visible-Light-Induced Organophotoredox-Catalyzed Phosphonylation of 2H-Indazoles with Diphenylphosphine Oxide

被引:92
作者
Singsardar, Mukta [1 ]
Dey, Amrita [1 ]
Sarkar, Rajib [1 ]
Hajra, Alakananda [1 ]
机构
[1] Visva Bharati, Dept Chem, Santini Ketan 731235, W Bengal, India
关键词
C-H FUNCTIONALIZATION; PHOTOREDOX CATALYSIS; DIARYLPHOSPHINE OXIDES; EFFICIENT SYNTHESIS; BOND FORMATION; ROSE-BENGAL; IMIDAZOHETEROCYCLES; INHIBITORS; DESIGN; WATER;
D O I
10.1021/acs.joc.8b02019
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free visible-light-induced phosphonylation of 2H-indazoles with diphenylphosphine oxide has been developed using rose bengal as an organophotoredox catalyst under ambient air at room temperature. A library of diphenyl(2-phenyl-2H-indazol-3-yl)phosphine oxide with broad functionalities has been synthesized in high yields. The experimental result suggests the radical pathway of the reaction.
引用
收藏
页码:12694 / 12701
页数:8
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  • [1] Visible Light Photocatalysis for the Generation and Use of Reactive Azolyl and Polyfluoroaryl Intermediates
    Arora, Amandeep
    Weaver, Jimmie D.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) : 2273 - 2283
  • [2] Design, Synthesis, and Functionalization of Imidazoheterocycles
    Bagdi, Avik Kumar
    Hajra, Alakananda
    [J]. CHEMICAL RECORD, 2016, 16 (04) : 1868 - 1885
  • [3] Synthesis of imidazo[1,2-a]pyridines: a decade update
    Bagdi, Avik Kumar
    Santra, Sougata
    Monir, Kamarul
    Hajra, Alakananda
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (09) : 1555 - 1575
  • [4] Direct Acyl Radical Addition to 2H-Indazoles Using Ag-Catalyzed Decarboxylative Cross-Coupling of α-Keto Acids
    Bogonda, Ganganna
    Kim, Hun Young
    Oh, Kyungsoo
    [J]. ORGANIC LETTERS, 2018, 20 (09) : 2711 - 2715
  • [5] Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization
    Condie, Allison G.
    Gonzalez-Gomez, Jose C.
    Stephenson, Corey R. J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) : 1464 - +
  • [6] Discovery of Pyrazolopyridones as a Novel Class of Gyrase B Inhibitors Using Structure Guided Design
    Cross, Jason B.
    Zhang, Jing
    Yang, Qingyi
    Mesleh, Michael F.
    Romero, Jan Antoinette C.
    Wang, Bin
    Bevan, Doug
    Poutsiaka, Katherine M.
    Epie, Felix
    Moy, Terence
    Daniel, Anu
    Shotwell, Joseph
    Chamberlain, Brian
    Carter, Nicole
    Andersen, Ole
    Barker, John
    Ryan, M. Dominic
    Metcalf, Chester A., III
    Silverman, Jared
    Nguyen, Kien
    Lippa, Blaise
    Dolle, Roland E.
    [J]. ACS MEDICINAL CHEMISTRY LETTERS, 2016, 7 (04): : 374 - 378
  • [7] Indazole estrogens:: Highly selective ligands for the estrogen receptor β
    De Angelis, M
    Stossi, F
    Carlson, KA
    Katzenellenbogen, BS
    Katzenellenbogen, JA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (04) : 1132 - 1144
  • [8] Paclitaxel, cisplatin and lonidamine in advanced ovarian cancer. A phase II study
    De Lena, M
    Lorusso, V
    Latorre, A
    Fanizza, G
    Gargano, G
    Caporusso, L
    Guida, M
    Catino, A
    Crucitta, E
    Sambiasi, D
    Mazzei, A
    [J]. EUROPEAN JOURNAL OF CANCER, 2001, 37 (03) : 364 - 368
  • [9] Merging Visible Light Photoredox Catalysis with Metal Catalyzed C-H Activations: On the Role of Oxygen and Superoxide Ions as Oxidants
    Fabry, David C.
    Rueping, Magnus
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) : 1969 - 1979
  • [10] Phosphine-Phosphinite and Phosphine-Phosphite Ligands: Preparation and Applications in Asymmetric Catalysis
    Fernandez-Perez, Hector
    Etayo, Pablo
    Panossian, Armen
    Vidal-Ferran, Anton
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 2119 - 2176