Electrochemical S-H and O-H insertion reactions from thiols or salicylic acids with diazo esters

被引:9
作者
He, Zhiqin [1 ]
Zhao, Wei [1 ]
Li, Yufeng [1 ]
Yu, Yang [3 ]
Huang, Fei [1 ,2 ]
机构
[1] Nanjing Normal Univ, Sch Food Sci & Pharmaceut Engn, Nanjing 210023, Peoples R China
[2] Nanjing Tech Univ, Sch Pharmaceut Sci, Nanjing 211816, Peoples R China
[3] Nanjing Tech Univ, Sch Environm Sci & Engn, Nanjing 211816, Peoples R China
基金
中国国家自然科学基金;
关键词
MODIFIED SEWAGE-SLUDGE; BOND INSERTION; CATALYZED INSERTION; VERSATILE SYNTHONS;
D O I
10.1039/d2ob01273a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An electrochemical carbenoid insertion reaction of diazo compounds into C-S and C-O bonds with electricity as the oxidant has been reported in this work. In this protocol, this transformation proceeded smoothly under mild conditions at room temperature in the absence of a catalyst and a ligand. In addition, the yield of the S-H insertion product was up to 96% and the O-H product could be efficiently obtained in up to 80% yield. Of note is that this environmentally friendly strategy exhibited excellent applicability in gram-scale synthesis.
引用
收藏
页码:8078 / 8082
页数:5
相关论文
共 36 条
[1]   Synthesis of Rhodium Complexes with Chiral Diene Ligands via Diastereoselective Coordination and Their Application in the Asymmetric Insertion of Diazo Compounds into E-H Bonds [J].
Ankudinov, Nikita M. ;
Chusov, Denis A. ;
Nelyubina, Yulia, V ;
Perekalin, Dmitry S. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (34) :18712-18720
[2]   US FDA Approved Drugs from 2015-June 2020: A Perspective [J].
Bhutani, Priyadeep ;
Joshi, Gaurav ;
Raja, Nivethitha ;
Bachhav, Namrata ;
Rajanna, Prabhakar K. ;
Bhutani, Hemant ;
Paul, Atish T. ;
Kumar, Raj .
JOURNAL OF MEDICINAL CHEMISTRY, 2021, 64 (05) :2339-2381
[3]   Borane-Catalyzed Stereoselective C-H Insertion, Cyclopropanation, and Ring-Opening Reactions [J].
Dasgupta, Ayan ;
Babaahmadi, Rasool ;
Slater, Ben ;
Yates, Brian F. ;
Ariafard, Alireza ;
Melen, Rebecca L. .
CHEM, 2020, 6 (09) :2364-2381
[4]   Photochemical O-H Functionalization of Aryldiazoacetates with Phenols via Proton Transfer [J].
Empel, Claire ;
Jana, Sripati ;
Pei, Chao ;
Thanh Vinh Nguyen ;
Koenigs, Rene M. .
ORGANIC LETTERS, 2020, 22 (18) :7225-7229
[5]   Reactions of 5-Aminoisoxazoles with α-Diazocarbonyl Compounds: Wolff Rearrangement vs N-H Insertion [J].
Ge, Yun ;
Sun, Wangbin ;
Chen, Yang ;
Huang, Yulin ;
Liu, Zhuang ;
Jiang, Yaojia ;
Loh, Teck-Peng .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (05) :2676-2688
[6]   Electrochemical Oxidative Carbon-Atom Difunctionalization: Towards Multisubstituted Imino Sulfide Ethers [J].
Guan, Zhipeng ;
Zhu, Shuxiang ;
Wang, Siyuan ;
Wang, Huamin ;
Wang, Siyuan ;
Zhong, Xingxing ;
Bu, Faxiang ;
Cong, Hengjiang ;
Lei, Aiwen .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (03) :1573-1577
[7]   Recent progress in insertion and cyclopropanation reactions of metal carbenoids from α-diazocarbonyl compounds [J].
Gurmessa, Getahun Tadesse ;
Singh, Girija Shankar .
RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (11) :6447-6504
[8]   Silver-Catalyzed Asymmetric Insertion into Phenolic O-H Bonds using Aryl Diazoacetates and Theoretical Mechanistic Studies [J].
Harada, Shingo ;
Tanikawa, Koki ;
Homma, Haruka ;
Sakai, Chigaya ;
Ito, Tsubasa ;
Nemoto, Tetsuhiro .
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (52) :12058-12062
[9]   Uncommon carbene insertion reactions [J].
Huang, Ming-Yao ;
Zhu, Shou-Fei .
CHEMICAL SCIENCE, 2021, 12 (48) :15790-15801
[10]   Electro-Oxidative S-H/S-H Cross-Coupling with Hydrogen Evolution: Facile Access to Unsymmetrical Disulfides [J].
Huang, Pengfei ;
Wang, Pan ;
Tang, Shan ;
Fu, Zhuangjiong ;
Lei, Aiwen .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (27) :8115-8119