Synthesis of thioesters using an electrochemical three-component reaction involving elemental sulfur

被引:1
|
作者
Liu, Gongbo [1 ]
Xu, Shuoyu [1 ]
Yue, Yangyang [1 ]
Su, Changhui [1 ]
Song, Wangze [1 ]
机构
[1] Dalian Univ Technol, Canc Hosp, Sch Chem, Sch Chem Engn, Dalian 116024, Peoples R China
基金
中国国家自然科学基金;
关键词
ORGANOCATALYZED ANODIC-OXIDATION; ALPHA-KETO ACIDS; ACYLATION;
D O I
10.1039/d4cc01910e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An electrochemical three-component reaction involving elemental sulfur is disclosed for achieving a metal-free, oxidant-free synthesis of thioesters in a high atom-economical, step-economical and chemoselective manner. A mechanistic investigation indicates that the use of elemental sulfur to trap acyl radical derived from radical umpolung of alpha-keto acid with an electrochemical design can efficiently generate a carbonyl thiyl radical, which can further be captured by diazoalkane to afford various thioesters. An electrochemical three-component reaction involving elemental sulfur is disclosed for achieving a metal-free, oxidant-free synthesis of thioesters in a high atom-economical, step-economical and chemoselective manner.
引用
收藏
页码:6154 / 6157
页数:4
相关论文
共 50 条
  • [1] A Novel Three-Component Reaction Involving Terminal Alkynes, Elemental Sulfur, and Strained Heterocycles
    Samzadeh-Kermani, Alireza
    SYNLETT, 2015, 26 (05) : 643 - 645
  • [2] Synthesis of Benzo[b]thiophenes through Rhodium-Catalyzed Three-Component Reaction using Elemental Sulfur
    Moon, Sanghun
    Kato, Moena
    Nishii, Yuji
    Miura, Masahiro
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (08) : 1669 - 1673
  • [3] Synthesis of thiophosphates through a three-component reaction by using sulfur dioxide as the sulfur source
    Gong, Xinxing
    Chen, Jiahao
    Liu, Jianhe
    Wu, Jie
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (11): : 2221 - 2225
  • [4] Copper-catalyzed three-component reaction to construct thietane ring using elemental sulfur
    Patel, Dixita J.
    Chikhalia, Kishor H.
    TETRAHEDRON, 2024, 166
  • [5] Three-component reaction between elemental sulfur, primary phosphines, and amines: straightforward synthesis of organylammonium trithiophosphonates
    Artem'ev, Alexander V.
    Malysheva, Svetlana F.
    Belogorlova, Nataliya A.
    Gusarova, Nina K.
    JOURNAL OF SULFUR CHEMISTRY, 2013, 34 (03) : 227 - 232
  • [6] Synthesis of benzisothiazoles by a three-component reaction using elemental sulfur and ammonium as heteroatom components under transition metal-free conditions
    Wang, Min
    Meng, Xia
    Cai, Changqun
    Wang, Lingyun
    Gong, Hang
    GREEN SYNTHESIS AND CATALYSIS, 2022, 3 (02): : 168 - 174
  • [7] Facile synthesis of sulfur-substituted allenes by a three-component reaction
    Huang, X
    Xiong, ZC
    TETRAHEDRON LETTERS, 2003, 44 (31) : 5913 - 5915
  • [8] Metal-free three-component synthesis of thioamides from β-nitrostyrenes, amines and elemental sulfur
    Peng, Ling
    Ma, Li
    Ran, Ying
    Chen, Yunfeng
    Zeng, Zhigang
    TETRAHEDRON LETTERS, 2021, 74
  • [9] Photocatalytic Activation of Elemental Sulfur Enables a Chemoselective Three-Component Thioesterification
    Murakami, Sho
    Nanjo, Takeshi
    Takemoto, Yoshiji
    ORGANIC LETTERS, 2021, 23 (19) : 7650 - 7655
  • [10] Three-component reaction of secondary phosphines with elemental selenium and amines
    A. V. Artem’ev
    N. K. Gusarova
    S. F. Malysheva
    B. A. Trofimov
    Russian Journal of Organic Chemistry, 2010, 46 : 592 - 593