Intramolecular oxidative coupling: I2/TBHP/NaN3-mediated synthesis of benzofuran derivatives

被引:16
|
作者
Xu, Wengang [1 ]
Li, Qingcui [1 ]
Cao, Chuanpeng [1 ]
Zhang, Fanglin [1 ]
Zheng, Hua [1 ]
机构
[1] Wuhan Univ Technol, Sch Chem Chem Engn & Life Sci, Wuhan 430070, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
ONE-POT SYNTHESIS; BOND FORMATION; O-ARYLPHENOLS; IODINE; DIBENZOFURANS; CYCLIZATION; 2-ARYLBENZOFURANS; ACTIVATION; ANNULATION; INHIBITORS;
D O I
10.1039/c5ob00577a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel intramolecular oxidative coupling reaction has been established to prepare benzofuran derivatives via direct C(sp(2))-H functionalization for the formation of C-O bond. This transformation is mediated by I-2/TBHP/NaN3 under metal-free conditions and a catalytic amount of NaN3 plays a crucial role in the reaction. Furthermore, the reaction tolerates a broad substrate scope with average to excellent yields.
引用
收藏
页码:6158 / 6161
页数:4
相关论文
共 50 条
  • [21] Synthesis of Amides from Aliphatic Acids and Amines by using of I2/TBHP at Room Temperature
    Sirgamalla, Rambabu
    Kommakula, Ashok
    Banoth, Sonyanaik
    Dharavath, Ravi
    Adem, Kurumanna
    Madhu, P.
    Boda, Sakram
    CHEMISTRYSELECT, 2018, 3 (04): : 1062 - 1065
  • [22] Intermolecular dearomative oxidative coupling of indoles with ketones and sulfonylhydrazines catalyzed by I2: synthesis of [2,3]-fused indoline tetrahydropyridazines
    Feng Wei
    Liang Cheng
    Hongyan Huang
    Jiejie Liu
    Dong Wang
    Li Liu
    Science China(Chemistry), 2016, 59 (10) : 1311 - 1316
  • [23] Intermolecular dearomative oxidative coupling of indoles with ketones and sulfonylhydrazines catalyzed by I2: synthesis of [2,3]-fused indoline tetrahydropyridazines
    Wei, Feng
    Cheng, Liang
    Huang, Hongyan
    Liu, Jiejie
    Wang, Dong
    Liu, Li
    SCIENCE CHINA-CHEMISTRY, 2016, 59 (10) : 1311 - 1316
  • [24] Intermolecular dearomative oxidative coupling of indoles with ketones and sulfonylhydrazines catalyzed by I2: synthesis of [2,3]-fused indoline tetrahydropyridazines
    Feng Wei
    Liang Cheng
    Hongyan Huang
    Jiejie Liu
    Dong Wang
    Li Liu
    Science China Chemistry, 2016, 59 : 1311 - 1316
  • [25] I2/TBHP-Mediated Oxidative Coupling of Amino-Based Bisnucleophiles and Isocyanides: Access to 2-Aminobenzoxazinones, 2-Aminobenzoxazines, and 2-Aminoquinazolines under Metal-Free Conditions
    Wang, Hong-Xia
    Wei, Tian-Qi
    Xu, Pei
    Wang, Shun-Yi
    Ji, Shun-Jun
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21): : 13491 - 13497
  • [26] Access to 2-Arylquinazolin-4(3H)-ones through Intramolecular Oxidative C(sp3)-H/N-H Cross-Coupling Mediated by I2/DMSO
    Wen, Simiaomiao
    Du, Yifan
    Liu, Yiwen
    Cui, Xiaofeng
    Liu, Qixing
    Zhou, Haifeng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (04)
  • [27] An oxidative cross-coupling reaction of 4-hydroxydithiocoumarin and amines/thiols using a combination of I2 and TBHP: access to lead molecules for biomedical applications
    Mahato, Karuna
    Arora, Neha
    Bagdi, Prasanta Ray
    Gattu, Radhakrishna
    Ghosh, Siddhartha Sankar
    Khan, Abu T.
    CHEMICAL COMMUNICATIONS, 2018, 54 (12) : 1513 - 1516
  • [28] BIOMIMETIC APPROACH TO BIFLAVONOIDS - OXIDATIVE COUPLING OF 2'-HYDROXYCHALCONES WITH I2 IN ALKALINE METHANOL
    ALI, SM
    ILYAS, M
    JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26): : 5415 - 5417
  • [29] I2/TBHP-mediated tandem cyclization and oxidation reaction: Facile access to 2,5-disubstituted oxazoles
    Guo, Xin
    Liu, Xianyan
    Li, Chonglong
    Jiang, Zhibo
    Nan, Zedong
    Liu, Yafeng
    TETRAHEDRON LETTERS, 2022, 112
  • [30] I2/TBHP- Mediated tandem cyclization and oxidation reaction: Facile access to 2-substituted thiazoles and benzothiazoles
    Liu, Li
    Tan, Chen
    Fan, Rong
    Wang, Zihan
    Du, Hongguang
    Xu, Kun
    Tan, Jiajing
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (02) : 252 - 256