Metal-Free Aerobic Sulfenyllactonization of Unsaturated Carboxylic Acids with Thiols Using Air as Sole Oxidant

被引:3
|
作者
Xiong, Yan-Shi [1 ]
Yu, Yang [1 ]
You, Yi-Peng [1 ]
Weng, Jiang [1 ]
Lu, Gui [1 ]
机构
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Prov Key Lab Chiral Mol & Drug Discover, Guangzhou 510006, Peoples R China
来源
CHEMISTRYSELECT | 2020年 / 5卷 / 25期
基金
中国国家自然科学基金;
关键词
Metal-free; Sulfenyllactonization; Radical; Difunctionalization; Carboxylic acids; ELECTROCATALYTIC APPROACH; CARBONYL-COMPOUNDS; ALKENES; PHOTOREDOX; STYRENES; OXYGEN; DIFUNCTIONALIZATION; BROMOLACTONIZATION; FUNCTIONALIZATION; CYCLIZATION;
D O I
10.1002/slct.202000542
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A metal-free aerobic sulfenyllactonization of unsaturated carboxylic acids with thiols has been disclosed. This method proceeded with air as the sole oxidant, without any metal catalyst, which provides an efficient access to a wide range of sulfenylated lactones with moderate to good yields. The operational simplicity, high atom efficiency, scalability and the use of bio-based green solvent under mild conditions are the attractive features of this methodology.
引用
收藏
页码:7382 / 7386
页数:5
相关论文
共 50 条
  • [1] Metal-free thioesterification of α,β-unsaturated aldehydes with thiols
    Bolt, Malgorzata
    Hanek, Kamil
    Zak, Patrycja
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (18) : 4846 - 4853
  • [2] Photochemical metal-free aerobic oxidation of thiols to disulfides
    Spiliopoulou, Nikoleta
    Kokotos, Christoforos G.
    GREEN CHEMISTRY, 2021, 23 (01) : 546 - 551
  • [3] Metal-free, aerobic ketooxygenations of alkenes using hydroxamic acids
    Schmidt, Valerie A.
    Alexanian, Erik J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [4] Metal-free, aerobic ketooxygenation of alkenes using hydroxamic acids
    Schmidt, Valerie A.
    Alexanian, Erik J.
    CHEMICAL SCIENCE, 2012, 3 (05) : 1672 - 1674
  • [5] Metal-Free, Aerobic Dioxygenation of Alkenes Using Hydroxamic Acids
    Schmidt, Valerie A.
    Alexanian, Erik J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (26) : 4491 - 4494
  • [6] Metal-Free Decarboxylative Cyanomethylation of β-Aryl/Heteroaryl Substituted α,β-Unsaturated Carboxylic Acids to γ-Ketonitriles
    Chand, Shiv
    Kumar, Saurabh
    Sharma, Anup Kumar
    Singh, Krishna Nand
    ORGANIC LETTERS, 2024, 26 (46) : 10051 - 10055
  • [7] Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions
    Jereb, Marjan
    Hribernik, Luka
    GREEN CHEMISTRY, 2017, 19 (09) : 2286 - 2295
  • [8] Metal-free amidation of carboxylic acids with tertiary amines
    Phakhodee, Wong
    Wangngae, Sirilak
    Pattarawarapan, Mookda
    RSC ADVANCES, 2016, 6 (65) : 60287 - 60290
  • [9] Metal-Free Electrocatalytic Aerobic Hydroxylation of Arylboronic Acids
    Luo, Jian
    Hu, Bo
    Sam, Alyssa
    Liu, T. Leo
    ORGANIC LETTERS, 2018, 20 (02) : 361 - 364
  • [10] Metal-Free Visible-Light-Mediated Oxidative Cross-Coupling of Thiols with P(O)H Compounds Using Air as the Oxidant
    Sun, Jian-Guo
    Yang, Hua
    Li, Ping
    Zhang, Bo
    ORGANIC LETTERS, 2016, 18 (19) : 5114 - 5117