A facile copper(I)-catalyzed homocoupling of terminal alkynes to 1,3-diynes with diaziridinone under mild conditions

被引：36
|
作者：
Zhu, Yingguang [1 ]
Shi, Yian [1 ]
机构：
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 43期
基金：
美国国家卫生研究院;
关键词：
CU(I)-CATALYZED REGIOSELECTIVE DIAMINATION; COUPLING REACTIONS; PD(0)-CATALYZED DIAMINATION; EFFICIENT SYNTHESIS; CONJUGATED DIENES; ASYMMETRIC DIAMINATION; COPPER HYDROXIDE; ROOM-TEMPERATURE; PALLADIUM; CATALYST;
D O I：
10.1039/c3ob41621f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and efficient Cu(I)-catalyzed oxidative homocoupling of terminal alkynes with diaziridinone as an oxidant is described. Various terminal alkynes can be transformed into the corresponding 1,3-diynes in good yields. The reaction process is base-free, operationally simple, and amenable to the gram scale.
引用
收藏
页码：7451 / 7454
页数：4
相关论文
共 50 条
  • [41] One-pot Synthesis of Alkynylated Coumarins via Rhodium-Catalyzed Annulation of Aryl Thiocarbamates with 1,3-Diynes or Terminal Alkynes
    Gao, Yuan
    Zeng, Fenfen
    Sun, Xudong
    Zeng, Minfeng
    Yang, Zhen
    Huang, Xianqiang
    Shen, Guodong
    Tan, Yongsheng
    Feng, Ruokun
    Qi, Chenze
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (07) : 1328 - 1333
  • [42] Nickel-Catalyzed Oxidative Coupling Reactions of Two Different Terminal Alkynes Using O2 as the Oxidant at Room Temperature: Facile Syntheses of Unsymmetric 1,3-Diynes
    Yin, Weiyan
    He, Chuan
    Chen, Mao
    Zhang, Heng
    Lei, Aiwen
    ORGANIC LETTERS, 2009, 11 (03) : 709 - 712
  • [43] Cu (I) immobilized on functionalized SBA-15: A recyclable catalyst for the synthesis of 1,3-diynes using terminal alkynes without base
    Ma, Zongyan
    Wang, Xiaoyu
    Wei, Shuoyun
    Yang, Honglei
    Zhang, Fengwei
    Wang, Peng
    Xie, Miao
    Ma, Jiantai
    CATALYSIS COMMUNICATIONS, 2013, 39 : 24 - 29
  • [44] Synthesis of 1,4-diarylsubstituted 1,3-diynes through ligand-free copper-catalyzed oxidative decarboxylative homocoupling of aryl propiolic acids
    Liu, De-Xian
    Li, Fei-Long
    Li, Hong-Xi
    Gao, Jun
    Lang, Jian-Ping
    TETRAHEDRON, 2014, 70 (14) : 2416 - 2421
  • [45] Copper(I)-Catalyzed Sulfenylation of 1,3-Dicarbonyl Substrates with Disulfides under Mild Conditions
    Zhao, Jingnan
    Yang, Fan
    Yu, Zongyi
    Tang, Xiaofei
    Wu, Yufeng
    Ma, Cunfei
    Meng, Qingwei
    SYNLETT, 2019, 30 (19) : 2181 - 2184
  • [46] A HIGHLY CONVENIENT AND GENERAL-METHOD FOR THE SYNTHESIS OF 1,4-DISUBSTITUTED 1,3-DIYNES FROM TERMINAL ALKYNES VIA PALLADIUM COPPER CATALYSIS
    KUNDU, NG
    PAL, M
    CHOWDHURY, C
    JOURNAL OF CHEMICAL RESEARCH-S, 1993, (10): : 432 - 433
  • [47] DFT Study on Copper-Catalyzed Hydroboration of 1,3-Diynes: Mechanism, Selectivity, and Comparison with Ruthenium
    Zhang, Lei
    Li, Shan
    Wen, Yanhui
    Ma, Xiaosi
    Zhang, Jie
    Zhou, Jianguo
    Meng, Xiangtai
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 14 (01)
  • [48] Cobalt(I)-catalyzed neutral Diels-Alder reactions of 1,3-diynes with acyclic 1,3-dienes
    Hilt, G
    Smolko, KI
    SYNTHESIS-STUTTGART, 2002, (05): : 686 - 692
  • [49] Catalytic enantioselective addition of terminal 1,3-diynes to aromatic ketones: facile access to chiral nonracemic tertiary alcohols
    Liu, Tian-Lin
    Ma, Hai
    Zhang, Fa-Guang
    Zheng, Yan
    Nie, Jing
    Ma, Jun-An
    CHEMICAL COMMUNICATIONS, 2011, 47 (48) : 12873 - 12875
  • [50] Ionic Liquid-Promoted Copper(II)-Catalyzed Homocoupling of Terminal Alkynes in Aqueous Phase or under Solvent-Limited Conditions
    Li, Shiguang
    Chen, Xi
    Chen, Jinping
    Gong, Hang
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2016, 89 (07) : 794 - 797
12345