Direct annulation between glycine derivatives and thiiranes through photoredox/iron cooperative catalysis

被引:8
|
作者
Wang, Shutao [1 ]
Zhang, Yuan [1 ]
Hu, Yansong [1 ]
Zhou, Jintao [1 ]
Chen, Zhidang [1 ]
Liu, Zhao [2 ]
Zhang, Yuan [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, 222 South Tianshui Rd, Lanzhou 730000, Peoples R China
[2] Lanzhou Univ, Hosp 1, Lanzhou, Peoples R China
关键词
OXIDATIVE C-SP3-H FUNCTIONALIZATION; ACCESS; ACID; ALKYLATION; ESTERS;
D O I
10.1039/d3cc04580c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A visible-light-induced aerobic oxidative [2+3] cycloaddition reaction between glycine derivatives and thiiranes has been disclosed, which provides an efficient and atom-economical strategy for the rapid synthesis of thiazolidine-2-carboxylic acid derivatives and the post-modification of glycine-derived dipeptides under mild conditions with good yield and high diastereoselectivities. A preliminary mechanistic study favors a pathway involving a cooperative photoredox catalysis and iron catalysis. A visible-light-induced aerobic oxidative [2+3] cycloaddition reaction between glycine derivatives and thiiranes is achieved via a cooperative photoredox catalysis and iron catalysis.
引用
收藏
页码:12783 / 12786
页数:4
相关论文
共 50 条
  • [21] Merging photoredox catalysis with transition metal catalysis: Direct C4-H amination of 8-hydroxyquinoline derivatives
    Ma, Yueyue
    Shi, Yaqi
    Yang, Fan
    Wu, Yusheng
    Wu, Yangjie
    TETRAHEDRON, 2019, 75 (29) : 3904 - 3910
  • [22] Selective radical cascade (4+2) annulation with olefins towards the synthesis of chroman derivatives via organo-photoredox catalysis
    Guan, Zhipeng
    Zhong, Xingxing
    Ye, Yayu
    Li, Xiangwei
    Cong, Hengjiang
    Yi, Hong
    Zhang, Heng
    Huang, Zhiliang
    Lei, Aiwen
    CHEMICAL SCIENCE, 2022, 13 (21) : 6316 - 6321
  • [23] Site-Selective O-Arylation of Carbohydrate Derivatives through Nickel-Photoredox Catalysis
    Jdanova, Sofia
    Guthrie, James G.
    Taylor, Mark S.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 90 (01): : 479 - 492
  • [24] Direct C-H Multifluoroarylation of Ethers through Hydrogen Atom Transfer Using Photoredox Catalysis
    Wang, Junlei
    Huang, Binbin
    Gao, Yuan
    Yang, Chao
    Xia, Wujiong
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11): : 6895 - 6903
  • [25] Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct α-Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis
    Twilton, Jack
    Christensen, Melodie
    DiRocco, Daniel A.
    Ruck, Rebecca T.
    Davies, Ian W.
    MacMillan, David W. C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (19) : 5369 - 5373
  • [26] Direct Aldehyde Csp2-H Functionalization through Visible-Light-Mediated Photoredox Catalysis
    Minh Duy Vu
    Das, Mrinmoy
    Liu, Xue-Wei
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (63) : 15899 - 15902
  • [27] Direct allylic acylation via cross-coupling involving cooperative N‑heterocyclic carbene, hydrogen atom transfer, and photoredox catalysis
    Xiaochen Wang
    Rongxin Yang
    Binbing Zhu
    Yuxiu Liu
    Hongjian Song
    Jianyang Dong
    Qingmin Wang
    Nature Communications, 14
  • [28] Directed γ-C(sp3)-H Alkylation of Carboxylic Acid Derivatives through Visible Light Photoredox Catalysis
    Chen, Dian-Feng
    Chu, Tjohn C. K.
    Rovis, Tomislav
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (42) : 14897 - 14900
  • [29] Modular and Practical 1,2-Aryl(Alkenyl) Heteroatom Functionalization of Alkenes through Iron/Photoredox Dual Catalysis
    Zhang, Weigang
    Liu, Tao
    Ang, Hwee Ting
    Luo, Penghao
    Lei, Zhexuan
    Luo, Xiaohua
    Koh, Ming Joo
    Wu, Jie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (44)
  • [30] Enantio- and Diastereoselective De Novo Synthesis of 3-Substituted Proline Derivatives via Cooperative Photoredox/Bronsted Acid Catalysis and Epimerization
    Che, Chao
    Lu, Yi-Nan
    Wang, Chun-Jiang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (05) : 2779 - 2786