Visible Light-Promoted C-C Bond Formation from Hydroxyaryls in Water

被引：3
|
作者：
Saporito, Dafne [1 ]
Rodriguez, Sergio A. [2 ]
Baumgartner, Maria T. [1 ]
机构：
[1] Univ Nacl Cordoba, Fac Ciencias Quim, INFIQC Dept Quim Organ, Ciudad Univ, RA-5000 Cordoba, Argentina
[2] Univ Nacl Santiago del Estero, Inst Ciencias Quim, CONICET, Fac Agron & Agroind, Av Belgrano Sur 1912, RA-4200 Santiago Del Estero, Argentina
来源：
AUSTRALIAN JOURNAL OF CHEMISTRY | 2019年 / 72卷 / 12期
关键词：
TRANSITION-METAL-FREE; DIFFERENT ROUTE; ARYLATION; S(RN)1; ELECTRON; ACIDS; HETEROCYCLES; CYCLIZATION; CARBAZOLES; COUMARINS;
D O I：
10.1071/CH19378
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An eco-friendly and direct arylation of hydroxyaryls in water using photoinduced reactions with different substrates (1-bromo-2-naphthol, 1-iodo-2-naphthol, N-(2-iodophenyl)acetamide, 5-bromouracil, 2-iodo-N-methylbenzamide, and 2-iodobenzamide) was studied. For example, p-expanded coumarins, compounds with potential optical applications, were synthesized in very high yield, without the use of toxic reagents, in a one-pot reaction. In addition, we demonstrate that the irradiation source (halogen lamp) can be efficiently replaced by an LED without altering the reaction yield.
引用
收藏
页码：978 / 982
页数：5
相关论文
共 50 条
  • [31] Visible-Light-Induced Difunctionalization of the C-C Bond of Alkylidenecyclopropanes with Acyl Chlorides
    Ding, Chuan
    Huang, Peng-Fei
    Xiong, Biquan
    Tang, Ke-Wen
    Liu, Yu
    CATALYSTS, 2023, 13 (06)
  • [32] Visible Light-Promoted Formation of C-B and C-S Bonds under Metal- and Photocatalyst-Free Conditions
    Blank, Lena
    Fagnoni, Maurizio
    Protti, Stefano
    Ruepin, Magnus
    SYNTHESIS-STUTTGART, 2019, 51 (05): : 1243 - 1252
  • [33] Remote C-C bond formation via visible light photoredox-catalyzed intramolecular hydrogen atom transfer
    Chen, Hui
    Yu, Shouyun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (24) : 4519 - 4532
  • [34] Visible light-promoted C-H functionalization of ethers and electron-deficient arenes
    Devari, Shekaraiah
    Shah, Bhahwal Ali
    CHEMICAL COMMUNICATIONS, 2016, 52 (07) : 1490 - 1493
  • [35] Singlet oxygen mediated dual C-C and C-N bond cleavage in visible light
    Ritu
    Sharma, Charu
    Kumar, Sharvan
    Jain, Nidhi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (15) : 2921 - 2928
  • [36] Focused study on palladium/nickel promoted decarbonylative C-C bond formation-minireview
    Roopan, Selvaraj Mohana
    ARKIVOC, 2022, : 238 - 256
  • [37] Iron-promoted C-C bond formation in the total synthesis of natural products and drugs
    Legros, Julien
    Figadere, Bruno
    NATURAL PRODUCT REPORTS, 2015, 32 (11) : 1541 - 1555
  • [38] Visible Light-promoted C(sp3)-H α-Carbamoylation of Cyclic Ethers with Isocyanides
    Russo, Camilla
    Volpe, Carmine
    Santoro, Federica
    Brancaccio, Diego
    Di Porzio, Anna
    Carotenuto, Alfonso
    Randazzo, Antonio
    Grimaud, Laurence
    Vitale, Maxime R.
    Protti, Stefano
    Giustiniano, Mariateresa
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (48)
  • [39] Visible light-promoted difluoromethylthiolation of aryldiazonium salts
    Wang W.
    Zhang S.
    Zhao H.
    Wang S.
    Wang, Wengui (chm_wangwg@ujn.edu.cn), 2018, Royal Society of Chemistry (16): : 8565 - 8568
  • [40] Catalytic C-C Bond Formation by C-H Functionaliza C-C Bond Cleavage Preface
    Dong, Guangbin
    TETRAHEDRON, 2016, 72 (22) : 2717 - 2717
12345