Synthesis of 2,3-Disubstituted 1,4-Naphthoquinones via Metal-Free C(sp2)-H Functionalization Followed by Suzuki Cross-Coupling Reactions

被引：7
|
作者：
Borah, Ashwini [1 ,2 ]
Sharma, Abhilash [1 ,2 ]
Hazarika, Hemanta [1 ,2 ]
Gogoi, Pranjal [1 ,2 ]
机构：
[1] CSIR, North East Inst Sci & Technol, Appl Organ Chem Grp, Chem Sci & Technol Div, Jorhat 785006, Assam, India
[2] Acad Sci & Innovat Res AcSIR, CSIR NEIST Campus, Jorhat, Assam, India
来源：
CHEMISTRYSELECT | 2017年 / 2卷 / 31期
关键词：
Benzoylation; C(sp2)-H Functionalization; Metal-free; 1,4-Naphthoquinone; Suzuki-Cross Coupling; C-H FUNCTIONALIZATION; FRIEDEL-CRAFTS ACYLATION; DIRECT ARYLATION; ARYL; NAPHTHOQUINONES; DERIVATIVES; QUINONES; PHOTOCHEMISTRY; IDENTIFICATION; GENERATION;
D O I：
10.1002/slct.201702404
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A synthetic strategy has been developed for the synthesis of 2,3-disubstituted-1,4-naphthoquinones. This synthetic protocol consists of metal-free tert-Butyl hydroperoxide (TBHP)-mediated oxidative benzoylation followed by Pd-catalyzed Suzukicross coupling reactions. Benzaldehyde, benzylalcohol and toluene were efficiently used as benzoyl radical source for the benzoylation of 1,4-naphthoquinones. By this protocol, a wide range of 1,4-naphthoquinones with different substitution patterns were efficiently prepared in a sequential way with good to excellent yields.
引用
收藏
页码：9999 / 10003
页数：5
相关论文
共 50 条
  • [41] Synthesis of Aryl Naphthoquinones and Maleimides via Pd(II)-Catalyzed Template-Assisted m-C(sp2)-H Functionalization Reaction
    Dutta, Ananya
    Jeganmohan, Masilamani
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (59)
  • [42] Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C-H and sp3 C-H bonds
    Kumar, Nivesh
    Ghosh, Santanu
    Bhunia, Subhajit
    Bisai, Alakesh
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 1153 - 1169
  • [43] TBN as a metal-free reagent initiated sp3 C-H functionalization of glycine esters: Synthesis of quinoline-2-carboxylate esters
    Liu, Xiaofei
    Shao, Yu
    Li, Pengfei
    Ji, Honghe
    Yuan, Yu
    Jia, Xiaodong
    TETRAHEDRON LETTERS, 2018, 59 (07) : 637 - 640
  • [44] A Palladium-Catalyzed Domino Approach to 2,3-Disubstituted Benzofurans via an Intermolecular Carbopalladation/C(sp3)-H Functionalization/Isomerization Sequence
    Boominathan, Siva Senthil Kumar
    Hou, Ruei-Jhih
    Hu, Wan-Ping
    Huang, Po-Jui
    Wang, Jeh-Jeng
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (18) : 2984 - 2989
  • [45] One-pot synthesis of indole-fused nitrogen heterocycles via the direct C(sp2)-H functionalization of naphthoquinones; accessibility for deep red emitting materials
    Kumari, Subramaniyan Prasanna
    Anthony, Savarimuthu Philip
    Ganesan, Subramaniapillai Selva
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (35) : 16874 - 16879
  • [46] Synthesis of α-Quaternary β-Lactams via Copper-Catalyzed Enantioconvergent Radical C(sp3)-C(sp2) Cross-Coupling with Organoboronate Esters
    Wang, Fu-Li
    Liu, Lin
    Yang, Chang-Jiang
    Luan, Cheng
    Yang, Jing
    Chen, Ji-Jun
    Gu, Qiang-Shuai
    Li, Zhong-Liang
    Liu, Xin-Yuan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (02)
  • [47] Electrochemically dehydrogenative C(sp2)-H/S-H cross-coupling: efficient synthesis of ortho-aminophenyl thioglycoside derivatives
    Hu, Li-Yan
    Zhu, Li
    Zhang, Shen-Yuan
    Guo, Yu-Xin
    Li, Yuan
    Zhu, Jie
    Wu, Lei
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (11) : 3041 - 3047
  • [48] Synthesis of benzosultams via an intramolecular sp2 C-H bond amination reaction of o-arylbenzenesulfonamides under metal-free conditions
    Li, Yuewen
    Ding, Qiuping
    Qiu, Guanyinsheng
    Wu, Jie
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (01) : 149 - 155
  • [49] Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp2)-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes
    Wang, Yidong
    Scrivener, Sarah G.
    Zuo, Xiao-Dong
    Wang, Ruihan
    Palermo, Philip N.
    Murphy, Ethan
    Durham, Austin C.
    Wang, Yi-Ming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (37) : 14998 - 15004
  • [50] Copper-Catalyzed C(sp3)-C(sp2) Cross-Coupling: Synthesis of 4-Aryl-2-alkylamino-3-nitro-4H-chromenes
    Rao, H. Surya Prakash
    Rao, A. Veera Bhadra
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) : 3646 - 3655
12345