Cu-Catalyzed Transformation of Alkynes and Alkenes with Azide and Dimethyl Sulfoxide Reagents

被引:77
作者
Shen, Tao [1 ]
Huang, Xiaoqiang [1 ]
Liang, Yu-Feng [1 ]
Jiao, Ning [1 ,2 ]
机构
[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
[2] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200062, Peoples R China
基金
中国国家自然科学基金;
关键词
PUMMERER REACTION CHEMISTRY; FACILE SYNTHESIS; BOND FORMATION; METHYL KETONES; EFFICIENT; STRATEGY; DMSO; NITROGENATION; OXIDATION; ACCESS;
D O I
10.1021/acs.orglett.5b03179
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and efficient Cu-catalyzed nitrogenation of alkynes and alkenes for the direct synthesis of sulfur-containing triazoles is described. Simple and readily available sulfoxides and azides are employed as the S- and N-source to prepare highly value N-,S-containing compounds from simple alkynes and alkenes.
引用
收藏
页码:6186 / 6189
页数:4
相关论文
共 71 条
  • [21] Copper(I)-Catalyzed Aerobic Oxidative Azide-Alkene Cycloaddition: An Efficient Synthesis of Substituted 1,2,3-Triazoles
    Janreddy, Donala
    Kavala, Veerababurao
    Kuo, Chun-Wei
    Chen, Wen-Chang
    Ramesh, Chintakunta
    Kotipalli, Trimurtulu
    Kuo, Ting-Shen
    Chen, Mei-Ling
    He, Chiu-Hui
    Yao, Ching-Fa
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (14-15) : 2918 - 2927
  • [22] Diaryl Sulfoxides from Aryl Benzyl Sulfoxides: A Single PalladiumCatalyzed Triple Relay Process
    Jia, Tiezheng
    Bellomo, Ana
    Montel, Sonia
    Zhang, Mengnan
    Baina, Kawtar E. L.
    Zheng, Bing
    Walsh, Patrick J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) : 260 - 264
  • [23] Palladium-Catalyzed Direct Arylation of Methyl Sulfoxides with Aryl Halides
    Jia, Tiezheng
    Bellomo, Ana
    El Baina, Kawtar
    Dreher, Spencer D.
    Walsh, Patrick J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (10) : 3740 - 3743
  • [24] A General Method for N-Methylation of Amines and Nitro Compounds with Dimethylsulfoxide
    Jiang, Xue
    Wang, Chao
    Wei, Yawen
    Xue, Dong
    Liu, Zhaotie
    Xiao, Jianliang
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (01) : 58 - 63
  • [25] Catalytic and direct methyl sulfonylation of alkenes and alkynes using a methyl sulfonyl radical generated from a DMSO, dioxygen and copper system
    Jiang, Yaojia
    Loh, Teck-Peng
    [J]. CHEMICAL SCIENCE, 2014, 5 (12) : 4939 - 4943
  • [26] A ONE-STEP PREPARATION OF ALPHA-AZIDO SULFONES FROM NITROCOMPOUNDS
    KOFT, ER
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) : 3466 - 3468
  • [27] Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO
  • [28] 2-5
  • [29] Metal-catalyzed carbon-sulfur bond formation
    Kondo, T
    Mitsudo, T
    [J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3205 - 3220
  • [30] Lahann J., 2009, CLICK CHEM BIOTECHNO, DOI DOI 10.1007/s11192-010-0202-z