Direct Alkynylation of Thiophenes: Cooperative Activation of TIPS-EBX with Gold and Bronsted Acids

被引:179
|
作者
Brand, Jonathan P. [1 ]
Waser, Jerome [1 ]
机构
[1] Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, EPFL SB ISIC LCSO, CH-1015 Lausanne, Switzerland
关键词
alkynes; cooperative catalysis; direct alkynylation; heterocycles; hypervalent iodine; CATALYZED DIRECT ALKYNYLATION; FIELD-EFFECT TRANSISTORS; DIRECT ARYLATION; HYPERVALENT IODINE; TERMINAL ALKYNES; COPPER; TRIFLUOROMETHYLATION; ETHYNYLATION; HETEROCYCLES; ARENES;
D O I
10.1002/anie.201003179
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
United we stand! Cooperative activation of the hypervalent-iodine reagent TIPS-EBX with a gold catalyst and a Brønsted acid allowed the first direct ethynylation of thiophenes at room temperature (see scheme; TFA = trifluoroacetic acid). The obtained ethynylthiophenes are important building blocks for organic dyes and electronic materials. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:7304 / 7307
页数:4
相关论文
共 8 条
  • [1] Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX
    Tolnai, Gergely L.
    Brand, Jonathan P.
    Waser, Jerome
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 745 - 749
  • [2] Isoxazole group directed Rh(III)-catalyzed alkynylation using TIPS-EBX
    Das, Sukanya
    Datta, Tanmoy
    Sk, Md. Abbasuddin
    Roy, Brindaban
    Nandi, Raj K.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (34) : 6922 - 6927
  • [3] C-H Alkynylation of N-Methylisoquinolone by Rhodium or Gold Catalysis: Theoretical Studies on the Mechanism, Regioselectivity, and Role of TIPS-EBX
    Zhao, Fengyue
    Xu, Benzhen
    Ren, Dongcheng
    Han, Lingli
    Yu, Zhangyu
    Liu, Tao
    ORGANOMETALLICS, 2018, 37 (06) : 1026 - 1033
  • [4] Zinc-gold cooperative catalysis for the direct alkynylation of benzofurans
    Li, Yifan
    Waser, Jerome
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 1763 - 1767
  • [5] Zinc Bis[bis(trimethylsilyl)amide] as an Efficient Lewis Acid/Bronsted Base Cooperative Catalyst for the Direct Alkynylation of Nitrones
    Saito, Yuki
    Yamashita, Yasuhiro
    Kobayashi, Shu
    CHEMISTRY LETTERS, 2015, 44 (07) : 976 - 977
  • [6] Alkyne activation with Bronsted acids, iodine, or gold complexes, and its fate leading to synthetic application
    Yamamoto, Yoshinori
    Gridnev, Ilya D.
    Patil, Nitin T.
    Jin, Tienan
    CHEMICAL COMMUNICATIONS, 2009, (34) : 5075 - 5087
  • [7] γ-Carbon Activation through N-Heterocyclic Carbene/Bronsted Acids Cooperative Catalysis: A Highly Enantioselective Route to δ-Lactams
    Xiao, Yonglong
    Wang, Jinxin
    Xia, Wenjing
    Shu, Shuangjie
    Jiao, Shenchao
    Zhou, Yu
    Liu, Hong
    ORGANIC LETTERS, 2015, 17 (15) : 3850 - 3853
  • [8] Dual Gold/Silver Catalysis Involving Alkynylgold(III) Intermediates Formed by Oxidative Addition and Silver-Catalyzed C-H Activation for the Direct Alkynylation of Cyclopropenes
    Yang, Yangyang
    Antoni, Patrick
    Zimmer, Marc
    Sekine, Kohei
    Mulks, Florian F.
    Hu, Long
    Zhang, Lumin
    Rudolph, Matthias
    Rominger, Frank
    Hashmi, A. Stephen K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (15) : 5129 - 5133