Direct C-H Alkylation of Naphthoquinone with Acetone and 1,3-Dicarbonyl Compounds via Radical Cross Dehydrogenation Coupling

被引:0
作者
Ou, Jiankang [1 ]
Liu, Haoyu [1 ]
Fang, Zeguo [1 ]
Zhang, Qian [1 ]
Li, Dong [1 ]
机构
[1] Hubei Univ Technol, Sch Mat & Chem Engn, New Mat & Green Mfg Talent Intro & Innovat Demonst, Wuhan 430068, Peoples R China
来源
CHEMISTRYSELECT | 2024年 / 9卷 / 28期
关键词
Alkylation; Naphthoquinone; Acetone; 1,3-Dicarbonyl compounds; Cross dehydrogenation coupling; METAL-FREE; QUINONES; FUNCTIONALIZATION; ARYLATION; DERIVATIVES; ROUTE;
D O I
10.1002/slct.202402061
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A direct C-H alkylation of naphthoquinones with acetone and 1,3-dicarbonyl compounds was developed to construct C-C bonds of alkyl-substituted naphthoquinone derivatives. It proceeded through an oxidative radical cross dehydrogenation coupling process under simple and mild conditions. This method provides a facile and efficient route for synthesis of functionalized naphthoquinones from readily available feedstocks. Construction of C-C bonds of alkyl-substituted naphthoquinones through C-H/C-H cross dehydrogenation coupling of naphthoquinones with acetone and 1,3-dicarbonyl compounds was developed. image
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页数:4
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共 42 条
  • [1] New, simple and selective synthesis of perfluoroalkylquinones by perfluoroalkyl radicals - Enthalpic and polar effects
    Antonietti, F
    Gambarotti, C
    Mele, A
    Minisci, F
    Paganelli, R
    Punta, C
    Recupero, F
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (20) : 4434 - 4440
  • [2] Brueggemeier R. W., 1996, J. Med. Chem, V39, P807
  • [3] Study of radical decarboxylation toward functionalization of naphthoquinones
    Commandeur, Claude
    Chalumeau, Celine
    Dessolin, Jean
    Laguerre, Michel
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (18) : 3045 - 3052
  • [4] Coppa F., 2006, Chem. Lett, V21, P1299
  • [5] Generation of Arylated Quinones by Iron-Catalyzed Oxidative Arylation of Phenols: Formal Synthesis of Phellodonin, Sarcodonin e, Leucomelone and Betulinan A
    Deb, Arghya
    Agasti, Soumitra
    Saboo, Tapish
    Maiti, Debabrata
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (04) : 705 - 710
  • [6] Iron-Catalyzed Direct C-H Arylation of Heterocycles and Quinones with Arylboronic Acids
    Deb, Arghya
    Manna, Srimanta
    Maji, Arun
    Dutta, Uttam
    Maiti, Debabrata
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) : 5251 - 5256
  • [7] Genotoxicity of plumbagin and its effects on catechol and NQNO-induced DNA damage in mouse lymphoma cells
    Demma, Jemal
    Hallberg, Karl
    Hellman, Bjoern
    [J]. TOXICOLOGY IN VITRO, 2009, 23 (02) : 266 - 271
  • [8] Direct Allylation of Quinones with Allylboronates
    Deng, Hong-Ping
    Wang, Dong
    Szabo, Kalman J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (06) : 3343 - 3348
  • [9] Tuning the redox potential of vitamin K3 derivatives by oxidative functionalization using a Ag(I)/GO catalyst
    El-Hout, S. I.
    Suzuki, H.
    El-Sheikh, S. M.
    Hassan, H. M. A.
    Harraz, F. A.
    Ibrahim, I. A.
    El-Sharkawy, E. A.
    Tsujimura, S.
    Holzinger, M.
    Nishina, Y.
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (63) : 8890 - 8893
  • [10] Silver-catalyzed cascade cyclization and functionalization of N-aryl-4-pentenamides: an efficient route to γ-lactam-substituted quinone derivatives
    Fang, Zeguo
    Xie, Lin
    Wang, Liang
    Zhang, Qian
    Li, Dong
    [J]. RSC ADVANCES, 2022, 12 (41) : 26776 - 26780