Transition-Metal-Free Oxidative Cross-Coupling of Methylhetarenes with Imidazoheterocycles towards Efficient C(sp2)-H Carbonylation

被引：21
|
作者：
Sultana, Faria [1 ]
Shaik, Siddiq Pasha [1 ,2 ]
Alarifi, Abdullah [3 ]
Srivastava, Ajay Kumar [1 ,2 ,4 ]
Kamal, Ahmed [1 ,2 ,3 ]
机构：
[1] CSIR Indian Inst Chem Technol, Med Chem & Biotechnol Div, Uppal Rd, Hyderabad 500007, Andhra Pradesh, India
[2] Acad Sci Innovat Res AcSIR, Div Chem Sci, New Delhi 110025, India
[3] King Saud Univ, Coll Sci, Dept Chem, Riyadh 11451, Saudi Arabia
[4] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Sect 10,Janakipuram Extens Sitapur Rd, Lucknow 226031, Uttar Pradesh, India
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 6卷 / 07期
关键词：
carbonylation; cross-coupling; green chemistry; heterocycles; oxidation; ONE-POT SYNTHESIS; C-H BONDS; DIMETHYL-SULFOXIDE; DIRECT ARYLATION; SELECTIVE METHOD; ANNULATION; PYRIDINES; CATALYST; ALKYNES; CYCLIZATION;
D O I：
10.1002/ajoc.201700173
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the oxidative cross-coupling of methylhetarenes with imidazoheterocycles by employing an eco-friendly iodine/DMSO reagent system has been developed. This C(sp(2))-H carbonylation reaction proceeds through an in situ oxidation of a methylhetarene into a formylhetarene followed by an oxidative cross-coupling reaction with an imidazoheterocycle. This method has a wide substrate scope and good functional group tolerance and enables the construction of a large number of carbonylated imidazoheterocycles in very good yields.
引用
收藏
页码：890 / 897
页数：8
相关论文
共 50 条
  • [31] Advances in C(sp2)-H/C(sp2)-H Oxidative Coupling of (Hetero)arenes Using 3d Transition Metal Catalysts
    Bansal, Sadhna
    Shabade, Anand B.
    Punji, Benudhar
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (08) : 1998 - 2022
  • [32] Transition-Metal-Free BF3-Mediated Oxidative and Non-Oxidative Cross-Coupling of Pyridines
    Chen, Quan
    Leon, Thierry
    Knochel, Paul
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (33) : 8746 - 8750
  • [33] Synthesis of α-aryl ketones through transition-metal-free cross-coupling
    Li, Xue
    Song, Qiuling
    NATURE SYNTHESIS, 2023, 2 (12): : 1138 - 1139
  • [34] Transition-Metal-Free Stereospecific Cross-Coupling with Alkenylboronic Acids as Nucleophiles
    Li, Chengxi
    Zhang, Yuanyuan
    Sun, Qi
    Gu, Tongnian
    Peng, Henian
    Tang, Wenjun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (34) : 10774 - 10777
  • [35] Asymmetric Organocatalytic Direct C(sp2)-H/C(sp3)-H Oxidative Cross-Coupling by Chiral Iodine Reagents
    Wu, Hua
    He, Yu-Ping
    Xu, Lue
    Zhang, Dong-Yang
    Gong, Liu-Zhu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (13) : 3466 - 3469
  • [36] Rhodium(III)-Catalyzed Oxidative Cross-Coupling of Unreactive C(sp3)-H Bonds with C(sp2)-H Bonds
    Tan, Guangying
    You, Jingsong
    ORGANIC LETTERS, 2017, 19 (18) : 4782 - 4785
  • [37] Regioselective Oxidative Trifluoromethylation of Imidazoheterocycles via C(sp2)-H Bond Functionalization
    Monir, Kamarul
    Bagdi, Avik Kumar
    Ghosh, Monoranjan
    Hajra, Alakananda
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03): : 1332 - 1337
  • [38] 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
  • [39] Photoinduced C(sp2)-H/C(sp2)-H Cross-Coupling of Alkenes: Direct Synthesis of 1,3-Dienes
    Xu, Qi
    Zheng, Baihui
    Zhou, Xiaoxuan
    Pan, Ling
    Liu, Qun
    Li, Yifei
    ORGANIC LETTERS, 2020, 22 (05) : 1692 - 1697
  • [40] Transition-Metal-Free Aryl-Aryl Cross-Coupling: C-H Arylation of 2-Naphthols with Diaryliodonium Salts
    Ghosh, Manoj K.
    Rzymkowski, Jan
    Kalek, Marcin
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (41) : 9619 - 9623
12345