An electron donor-acceptor photoactivation strategy for the synthesis of S -aryl dithiocarbamates using thianthrenium salts under mild aqueous micellar conditions

被引:69
作者
Xu, Hao [1 ]
Li, Xufeng [2 ]
Ma, Jie [1 ]
Zuo, Junze [1 ]
Song, Xiuyan [1 ]
Lv, Jian [1 ]
Yang, Daoshan [1 ,3 ]
机构
[1] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, MOE, Key Lab Opt Elect Sensing & Analyt Chem Life Sci, Qingdao 266042, Peoples R China
[2] Zhejiang Wansheng Co Ltd, Linhai 317000, Peoples R China
[3] Tsinghua Univ, Minist Educ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China
基金
中国国家自然科学基金;
关键词
S -Aryl dithiocarbamates; Visible-light; EDA complex; Thianthrenium salts; Micellar photocatalysis; PHOTOREDOX CATALYSIS; BORONIC ACIDS; WATER; FUNCTIONALIZATION; ACTIVATION; DISULFIDE; ARYLATION; HALIDES; AMINES;
D O I
10.1016/j.cclet.2023.108403
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An eco-friendly and convenient method is developed herein for the synthesis of S-aryl dithiocarba-mates via visible-light-induced SET process of an EDA complex between thianthrenium salt functional-ized arenes and dithiocarbamate anions under mild aqueous micellar conditions. This strategy indirectly realizes the method for constructing S-aryl dithiocarbamates through site-selective C -H functionaliza-tion of arenes. Most importantly, the reaction proceeded smoothly without addition of any photocatalyst, and the by-product thianthrene is recycled in quantity, ultimately minimizing the production of chemical waste. This protocol provides a promising synthesis candidate for the construction of valuable S-aryl dithiocarbamates, which also opens up a new avenue for micellar photocatalysis.& COPY; 2023 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
引用
收藏
页数:7
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共 85 条
[1]   Site-Selective C-H Functionalization-Sulfination Sequence to Access Aryl Sulfonamides [J].
Alvarez, Eva Maria ;
Plutschack, Matthew B. ;
Berger, Florian ;
Ritter, Tobias .
ORGANIC LETTERS, 2020, 22 (12) :4593-4596
[2]   Metal-free photoredox-catalysed formal C-H/C-H coupling of arenes enabled by interrupted Pummerer activation [J].
Aukland, Miles H. ;
Siauciulis, Mindaugas ;
West, Adam ;
Perry, Gregory J. P. ;
Procter, David J. .
NATURE CATALYSIS, 2020, 3 (02) :163-169
[3]   Targeting microbial resistance: Synthesis, antibacterial evaluation, DNA binding and modeling study of new chalcone-based dithiocarbamate derivatives [J].
Ayman, Marwa ;
El-Messery, Shahenda M. ;
Habib, Elsayed E. ;
Al-Rashood, Sara T. ;
Almehizia, Abdulrahman A. ;
Alkahtani, Hamad M. ;
Hassan, Ghada S. .
BIOORGANIC CHEMISTRY, 2019, 85 :282-292
[4]   Chemical and Medicinal Versatility of Dithiocarbamates: An Overview [J].
Bala, Veenu ;
Gupta, Gopal ;
Sharma, Vishnu L. .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2014, 14 (12) :1021-1032
[5]   Site-selective and versatile aromatic C-H functionalization by thianthrenation [J].
Berger, Florian ;
Plutschack, Matthew B. ;
Riegger, Julian ;
Yu, Wanwan ;
Speicher, Samira ;
Ho, Matthew ;
Frank, Nils ;
Ritter, Tobias .
NATURE, 2019, 567 (7747) :223-228
[6]   Carbamoyl Radical-Mediated Synthesis and Semipinacol Rearrangement of b-Lactam Diols [J].
Betou, Marie ;
Male, Louise ;
Steed, Jonathan W. ;
Grainger, Richard S. .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (21) :6505-6517
[7]   One-pot copper nanoparticle-catalyzed synthesis of S-aryl- and S-vinyl dithiocarbamates in water: high diastereoselectivity achieved for vinyl dithiocarbamates [J].
Bhadra, Sukalyan ;
Saha, Amit ;
Ranu, Brindaban C. .
GREEN CHEMISTRY, 2008, 10 (11) :1224-1230
[8]   Aryne Three-Component Coupling Involving CS2 for the Synthesis of S-Aryl Dithiocarbamates [J].
Bhattacharjee, Subrata ;
Deswal, Shiksha ;
Manoj, Niket ;
Jindal, Garima ;
Biju, Akkattu T. .
ORGANIC LETTERS, 2021, 23 (23) :9083-9088
[9]   Micellar Catalysis as a Tool for C-H Bond Functionalization toward C-C Bond Formation [J].
Borrego, Elena ;
Caballero, Ana ;
Perez, Pedro J. .
ORGANOMETALLICS, 2022, 41 (22) :3084-3098
[10]   Exploring the Structural Requirements for Inhibition of the Ubiquitin E3 Ligase Breast Cancer Associated Protein 2 (BCA2) as a Treatment for Breast Cancer [J].
Brahemi, Ghali ;
Kona, Fathima R. ;
Fiasella, Annalisa ;
Buac, Daniela ;
Soukupova, Jitka ;
Brancale, Andrea ;
Burger, Angelika M. ;
Westwell, Andrew D. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (07) :2757-2765