Zinc-gold cooperative catalysis for the direct alkynylation of benzofurans

被引:47
|
作者
Li, Yifan [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
alkynylation; benzofurans; cooperative catalysis; direct functionalization; gold catalysis; hypervalent iodine; HYPERVALENT IODINE REAGENTS; BENZIODOXOLONES; ACTIVATION; THIOPHENES;
D O I
10.3762/bjoc.9.204
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The direct alkynylation of benzofurans was achieved for the first time using the hypervalent iodine reagent 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) based on the cooperative effect between a gold catalyst and a zinc Lewis acid. High selectivity was observed for C2-alkynylation of benzofurans substituted with alkyl, aryl, halogen and ether groups. The reaction was also successful in the case of the more complex drug 8-methoxypsoralen (8-MOP).
引用
收藏
页码:1763 / 1767
页数:5
相关论文
共 50 条
  • [41] Direct alkylation of heteroarenes with unactivated bromoalkanes using photoredox gold catalysis
    McCallum, T.
    Barriault, L.
    CHEMICAL SCIENCE, 2016, 7 (07) : 4754 - 4758
  • [42] Cooperative catalysis by Ru and Pd for the direct coupling of a chelating aldehyde with iodoarenes or organostannanes
    Ko, S
    Kang, B
    Chang, S
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) : 455 - 457
  • [43] Enantioselective Alkynylation of 2-Aryl-3H-indol-3-ones via Cooperative Catalysis of Copper/Chiral Phosphoric Acid
    Wu, Xi-Xi
    Ma, Tao
    Qiao, Xiu-Xiu
    Zou, Chang-Peng
    Li, Ganpeng
    He, Yonghui
    Zhao, Xiao-Jing
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (18)
  • [44] COOPERATIVE ZINC ION-BASE CATALYSIS OF CARBONYL ADDITION-REACTIONS - HYDRATION
    MCDONALD, RS
    MACNEILL, JL
    BOUCHER, MT
    MARTIN, EV
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 : 370 - ORGN
  • [45] Catalytic Asymmetric Umpolung Tandem Reactions of Hemiacetals via Dinuclear Zinc Cooperative Catalysis
    Xing, Sheng-Nan
    Hua, Yuan-Zhao
    Yang, Xiao-Chao
    Du, Si-Si
    Jia, Shi-Kun
    Mei, Guang-Jian
    Wang, Min-Can
    ORGANIC LETTERS, 2022, 24 (22) : 3909 - 3914
  • [46] Cooperative Catalysis of p-Aminophenol and Titanocene Dichloride in Direct Mannich Reactions with Acetone
    Zhu, Xuyang
    Chen, Chun
    Yu, Binxun
    Zhang, Guofang
    Zhang, Weiqiang
    Gao, Ziwei
    CHEMISTRY LETTERS, 2014, 43 (12) : 1832 - 1834
  • [47] Direct Carbohydroxylation of Arylalkenes with Allylic Alcohols: Cooperative Catalysis of Copper, Silver, and a Bronsted Acid
    Ahmed, Waqar
    Zhang, Sheng
    Yu, Xiaoqiang
    Feng, Xiujuan
    Yamamoto, Yoshinori
    Bao, Ming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (08) : 2495 - 2499
  • [48] Direct Annulation between Aryl Iodides and Epoxides through Palladium/Norbornene Cooperative Catalysis
    Li, Renhe
    Dong, Guangbin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (06) : 1697 - 1701
  • [49] Direct annulation between glycine derivatives and thiiranes through photoredox/iron cooperative catalysis
    Wang, Shutao
    Zhang, Yuan
    Hu, Yansong
    Zhou, Jintao
    Chen, Zhidang
    Liu, Zhao
    Zhang, Yuan
    CHEMICAL COMMUNICATIONS, 2023, 59 (85) : 12783 - 12786
  • [50] Desymmetrization and Parallel Kinetic Resolution of 1-Ethynylcyclobutanols via Asymmetric Cooperative Gold Catalysis
    Zhao, Ke
    Yang, Ziguang
    Yang, Jielin
    Li, Xinyi
    Quintanilla, Carlos D.
    Zhang, Liming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (50) : 27205 - 27210