Sulfur-mediated difunctionalization of internal and terminal alkynes for the synthesis of α-acetoxy ketones

被引:8
|
作者
Zhang, Zhong [1 ,2 ]
Li, Pingfan [1 ]
机构
[1] Beijing Univ Chem Technol, Coll Chem, Beijing 100029, Peoples R China
[2] Shandong Univ, State Key Lab Microbial Technol, Qingdao 266237, Shandong, Peoples R China
基金
中国国家自然科学基金;
关键词
Activated sulfoxides; Difunctionalization of alkynes; Triflic anhydrides; alpha-Acetoxy ketones; INTERRUPTED PUMMERER REACTION; C-H ALKYLATION; SULFOXIDE; ARYLATION; OXIDATION; EFFICIENT; CONVENIENT; ARENES;
D O I
10.1016/j.tetlet.2020.151707
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The sulfur-mediated difunctionalization of alkynes is reported to give alpha-acetoxy ketones in a one-pot operation under mild conditions with 19-92% yield. By using wet potassium acetate as both the aqueous base and nucleophilic reagent, both terminal alkynes and internal alkynes could be converted into the alpha-acetoxy ketone products. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数:3
相关论文
共 50 条
  • [41] Photoredox-Mediated Synthesis of Functionalized Sulfoxides from Terminal Alkynes
    Kumar, Jaswant
    Ahmad, Ajaz
    Rizvi, Masood Ahmad
    Ganie, Majid Ahmed
    Khajuria, Chhavi
    Shah, Bhahwal Ali
    ORGANIC LETTERS, 2020, 22 (14) : 5661 - 5665
  • [42] Zinc mediated activation of terminal alkynes: stereoselective synthesis of alkynyl glycosides
    Tatina, Madhu Babu
    Kusunuru, Anil Kumar
    Yousuf, Syed Khalid
    Mukherjee, Debaraj
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (40) : 7900 - 7903
  • [43] Ru-mediated selective addition reactions of carboxylic acids to internal and terminal alkynes
    Karabulut, Solmaz
    Ozturk, Bengi Ozgun
    Imamoglu, Yavuz
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2010, 695 (19-20) : 2161 - 2166
  • [44] Amino Acid-Catalyzed Direct Synthesis of β-Keto Sulfones via Aerobic Difunctionalization of Terminal Alkynes in an Aqueous Medium
    Kumar, Navaneet
    Kumar, Atul
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (10) : 9182 - 9188
  • [45] Facile synthesis of elemental sulfur-mediated fluorine-containing covalent triazine frameworks and their performance in lithium-sulfur batteries
    Wang, Shuhao
    Song, Yue
    Wang, Zhao
    Xie, Wei
    Zhang, Shuran
    Yao, Chan
    Zhao, Yanning
    Xu, Yanhong
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (14) : 6951 - 6957
  • [46] Bismuth(III)-Catalyzed Hydration of Terminal Alkynes: Sustainable Synthesis of Methyl Ketones in Batch and Flow
    Otvos, Sandor B.
    Szecsenyi, Zsanett
    Fulop, Ferenc
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (15): : 13286 - 13293
  • [47] Gold-Catalyzed Intermolecular Oxidation of Terminal Alkynes: Simple and Efficient Synthesis of α-Mesyloxy Ketones
    Xie, Longyong
    Liang, Zhiwu
    Yan, Dong
    He, Weimin
    Xiang, Jiannan
    SYNLETT, 2013, 24 (14) : 1809 - 1812
  • [48] Highly efficient AgBF4-catalyzed synthesis of methyl ketones from terminal alkynes
    Chen, Zheng-Wang
    Ye, Dong-Nai
    Qian, Yi-Ping
    Ye, Min
    Liu, Liang-Xian
    TETRAHEDRON, 2013, 69 (30) : 6116 - 6120
  • [49] Highly Efficient Copper-Catalyzed Synthesis of Internal Alkynes via Aerobic Oxidative Arylation of Terminal Alkynes
    Rao, Honghua
    Fu, Hua
    Jiang, Yuyang
    Zhao, Yufen
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) : 458 - 462
  • [50] Sulfur-Mediated Mechanochemical Synthesis of Spherical and Needle-Like Copper Sulfide Nanocrystals with Antibacterial Activity
    Shalabayev, Zh
    Balaz, M.
    Daneu, N.
    Dutkova, E.
    Bujnakova, Z.
    Kanuchova, M.
    Dankova, Z.
    Balazova, L.
    Urakaev, F.
    Tkacikova, L.
    Burkitbayev, M.
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (15) : 12897 - 12909