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
  • [31] Electrochemical Cross-Coupling of C(sp2)-H with Aryldiazonium Salts via a Paired Electrolysis: an Alternative to Visible Light Photoredox-Based Approach
    Jiang, Yang-ye
    Dou, Gui-yuan
    Zhang, Luo-sha
    Xu, Kun
    Little, R. Daniel
    Zeng, Cheng-chu
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (22) : 5170 - 5175
  • [32] Rongalite induced metal-free C(sp2)-H functionalization of indoles: direct access to 3-(sulfonylmethyl) indoles
    Thunga, Sanjeeva
    Singh, Neetika
    Inapanuri, Madhu
    Kokatla, Hari Prasad
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (44) : 8787 - 8792
  • [33] Metal-Free 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-Mediated Cross-Dehydrogenative-Coupling (CDC) of Benzylic C(sp3)-H Bonds and Vinylic C(sp2)-H Bonds: Efficient One-Pot Synthesis of 1H-Indenes
    Wang, He
    Zhao, Yu-Long
    Li, Lei
    Li, Sha-Sha
    Liu, Qun
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) : 3157 - 3163
  • [34] Synthesis of biheteroaryls via 2-methyl quinoline C(sp3)-H functionalization under metal-free conditions
    Wang, Dahan
    Yang, Yuhan
    Xiao, Fuhong
    Liu, Jinbing
    Mao, Guojiang
    Deng, Guo-Jun
    GREEN SYNTHESIS AND CATALYSIS, 2024, 5 (01): : 73 - 76
  • [35] Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- and Alkynylnaphthoquinones and Derivatives
    Demidoff, Felipe C.
    Rodrigues Filho, Eduardo Jose P.
    de Souza, Andrea Luzia F.
    Netto, Chaquip D.
    de Carvalho, Leandro L.
    SYNTHESIS-STUTTGART, 2021, 53 (21): : 4097 - 4109
  • [36] Metal-free late-stage C(sp2)-H functionalization of N-aryl amines with various sodium salts
    Mudithanapelli, Chandrashekar
    Kim, Mi-hyun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (03) : 450 - 464
  • [37] Metal-free, visible-light-induced C(sp2)-H functionalization/C-O bond formation for the synthesis of flavones using air as an oxidant
    Bai, Yuntao
    Yang, Manqiang
    Lin, Shao-Xia
    Borse, Rahul Anil
    Thoke, Mahesh Bhagwan
    Yuan, Daqiang
    TETRAHEDRON LETTERS, 2023, 121
  • [38] Metal-free cascade oxidative decarbonylative alkylarylation of acrylamides with aliphatic aldehydes: a convenient approach to oxindoles via dual C(sp2)-H bond functionalization
    Yang, Luo
    Lu, Wen
    Zhou, Wang
    Zhang, Feng
    GREEN CHEMISTRY, 2016, 18 (10) : 2941 - 2945
  • [39] NIS Mediated Cross-Coupling of C(sp2)-H and N-H Bonds: A Transition-Metal-Free Approach toward Indolo[1,2-a]quinazolinones
    Badigenchala, Sindhura
    Sekar, Govindasamy
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (14) : 7657 - 7665
  • [40] Metal-Free α-C(sp3)-H Aroylation of Amines via a Photoredox Catalytic Radical-Radical Cross-Coupling Process
    Xu, Guo-Qiang
    Xiao, Teng-Fei
    Feng, Guo-Xuan
    Liu, Chen
    Zhang, Baoxin
    Xu, Peng-Fei
    ORGANIC LETTERS, 2021, 23 (08) : 2846 - 2852
12345