A three-component iodine-catalyzed oxidative coupling reaction: a heterodifunctionalization of 3-methylindoles

被引:3
|
作者
Zhang, Wei [1 ,2 ]
Xiang, Shiqun [2 ]
Fan, Weibin [2 ]
Jin, Jiang [2 ]
Li, Yinghua [2 ]
Huang, Deguang [1 ,2 ]
机构
[1] Fujian Normal Univ, Coll Chem & Mat Sci, Fuzhou 350007, Peoples R China
[2] Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Fujian, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H FUNCTIONALIZATION; ELECTRON-RICH HETEROCYCLES; FRIEDEL-CRAFTS ALKYLATION; METAL-FREE SULFENYLATION; 3-SUBSTITUTED INDOLES; 2,3-DISUBSTITUTED INDOLES; CONTROLLABLE SYNTHESIS; PHOTOREDOX CATALYSIS; CARBONYL-COMPOUNDS; ALPHA;
D O I
10.1039/d1ob00730k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free method for the synthesis of heterodifunctional indole derivatives is developed through TBHP/KI-mediated oxidative coupling. The reaction constructs C-O and C-C bonds in succession with the help of tert-butyl peroxy radicals generated by the TBHP/KI catalytic system, enabling the direct realization of the heterodifunctionalization of indole in one pot. The product of this reaction is a novel heterodifunctional compound. This work might provide a new effective method for the synthesis of polycyclic indole compounds.
引用
收藏
页码:5794 / 5799
页数:6
相关论文
共 50 条
  • [21] Ni-CATALYZED THREE-COMPONENT COUPLING OF 4-METHYLENE-2-OXAZOLIDINONES, ALKYNES, AND TRIMETHYLALUMINUM
    Yamahira, Tatsuya
    Ninokata, Ryo
    Onodera, Gen
    Kimura, Masanari
    HETEROCYCLES, 2017, 95 (02) : 722 - 729
  • [22] α-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones
    Tan, Liquan
    Chen, Cui
    Liu, Weibing
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 1079 - 1084
  • [23] N-Heterocyclic Carbene-Catalyzed Three-Component Domino Reaction of Alkynyl Aldehydes with Oxindoles
    Du, Ding
    Hu, Zhongyuan
    Jin, Jianlin
    Lu, Yingyan
    Tang, Weifang
    Wang, Bo
    Lu, Tao
    ORGANIC LETTERS, 2012, 14 (05) : 1274 - 1277
  • [24] N-Heterocyclic Carbene-Catalysed Mukaiyama-Michael Reaction and Mukaiyama Aldol/Mukaiyama-Michael Three-Component Coupling Reaction
    Nguyen, Kim
    Lupton, David W.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2017, 70 (04) : 436 - 441
  • [25] Synthesis of 3-(hydroxymethyl)-3-indol-3′-yloxindoles via Rh(II)-catalyzed three-component reaction of 3-diazooxindoles, indoles and formalin
    Jing, Changcheng
    Xing, Dong
    Wang, Chengjin
    Hu, Wenhao
    TETRAHEDRON, 2015, 71 (22) : 3597 - 3602
  • [26] A NOVEL THREE-COMPONENT COUPLING REACTION OF ARYNES, ISOCYANIDES, AND CYANOFORMATES: A STRAIGHTFORWARD ACCESS TO CYANO-SUBSTITUTED IMINOISOBENZOFURANS
    Li, Jing
    Noyori, Shintaro
    Iwasaki, Masayuki
    Nakajima, Kiyohiko
    Nishihara, Yasushi
    HETEROCYCLES, 2012, 86 (02) : 933 - 940
  • [27] Nickel-catalyzed regio- and diastereoselective intermolecular three-component coupling of oxabicyclic alkenes with alkynes and organoboronic acids
    Mannathan, Subramaniyan
    Cheng, Chien-Hong
    CHEMICAL COMMUNICATIONS, 2013, 49 (15) : 1557 - 1559
  • [28] Synthesis of substituted pyrroles via ultrasound assisted three-component coupling reaction of amines, α, β-unsaturated aldehydes and nitroalkanes
    Xiao, YS
    Wang, YG
    CHINESE JOURNAL OF CHEMISTRY, 2003, 21 (05) : 562 - 565
  • [29] Visible-light-promoted organic-dye-catalyzed three-component coupling of aldehydes, hydrazines and bromodifluorinated reagents
    Li, Jin-Xue
    Li, Lei
    Zhou, Ming-Dong
    Wang, He
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (06): : 1003 - 1007
  • [30] Synthesis of 3-indole derivatives by copper sulfonato Salen catalyzed three-component reactions in water
    Qu, Yanyang
    Ke, Fang
    Zhou, Li
    Li, Zhengkai
    Xiang, Haifeng
    Wu, Di
    Zhou, Xiangge
    CHEMICAL COMMUNICATIONS, 2011, 47 (13) : 3912 - 3914