Pyreneacyl sulfides as a visible light-induced versatile ligation platform

被引:23
作者
Tuten, Bryan T. [1 ,2 ,3 ]
Menzel, Jan P. [1 ,2 ,3 ]
Pahnke, Kai [1 ,2 ]
Blinco, James P. [1 ,3 ]
Barner-Kowollik, Christopher [1 ,2 ,3 ]
机构
[1] Karlsruhe Inst Technol, Inst Tech Chem & Polymerchem, Preparat Macromol Chem, Engesserstr 18, D-76128 Karlsruhe, Germany
[2] Karlsruhe Inst Technol, Inst Biol Grenzflachen, Hermann von Helmholtz Pl 1, D-76344 Eggenstein Leopoldshafen, Germany
[3] Queensland Univ Technol, Sch Chem Phys & Mech Engn, 2 George St, Brisbane, Qld 4000, Australia
关键词
PHOTO-GENERATED THIOALDEHYDES; ELECTRON-TRANSFER; CHEMISTRY; THIOBENZALDEHYDE; PHOTOCHEMISTRY; CYCLOADDITION; DESIGN; OXIDES;
D O I
10.1039/c7cc00711f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report a visible light responsive moiety capable of generating highly reactive thioaldehydes. Upon irradiation with visible light (420 nm) the pyreneacyl sulfide species undergoes a Norrish II elimination yielding thioaldehydes capable of being trapped by nucleophiles (amines, aminoxys, and thiols), as well as Diels-Alder processes, representing a new versatile ligation platform.
引用
收藏
页码:4501 / 4504
页数:4
相关论文
共 50 条
  • [31] Visible light-induced hydrogen atom transfer trifluoromethylthiolation of aldehydes with bismuth catalyst
    Dong, Jun
    Tang, Zhuang
    Zou, Luqian
    Zhou, Yongyun
    Chen, Jingchao
    CHEMICAL COMMUNICATIONS, 2024, 60 (06) : 742 - 745
  • [32] Visible Light-Induced Regioselective Cycloaddition of Benzoyl Azides and Alkenes To Yield Oxazolines
    Bellotti, Peter
    Brocus, Julien
    El Orf, Fatima
    Selkti, Mohamed
    Koenig, Burkhard
    Belmont, Philippe
    Brachet, Etienne
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10) : 6278 - 6285
  • [33] Visible Light-Induced Three-Component Alkoxyalkylation of Alkenes with α-Halocarbonyls and Alcohols
    Chowdhury, Soumyadeep Roy
    Kim, Hun Young
    Oh, Kyungsoo
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (23) : 17621 - 17634
  • [34] Visible Light-Induced Synthesis of Sulfenamides via Oxidative Coupling of Amines with Thiols
    Li, Yifan
    Yang, Wenjing
    Chen, Shuicai
    Zhou, Cong-Ying
    Guo, Zhen
    ORGANIC LETTERS, 2025,
  • [35] Visible light-induced Mallory reaction of tertiary benzanilides via iminium intermediates
    Ma, Xiaoqiang
    Wang, Si
    Tang, Zhanyong
    Huang, Jialin
    Jia, Tianhao
    Zhao, Xingda
    Zhao, Depeng
    CHEMICAL SCIENCE, 2024, 15 (41) : 17210 - 17216
  • [36] Visible light-induced 4-phenylthioxanthone-catalyzed aerobic oxidation of triarylphosphines
    Ding, Aishun
    Li, Shijie
    Chen, Yang
    Jin, Ruiwen
    Ye, Cong
    Hu, Jianhua
    Guo, Hao
    TETRAHEDRON LETTERS, 2018, 59 (43) : 3880 - 3883
  • [37] α,ω-Reactive Building Blocks Based on a Dual Functional RAFT Agent for Thermal and Light-Induced Ligation
    Langer, Marcel
    Mueller, Jan O.
    Goldmann, Anja S.
    Schacher, Felix H.
    Barner-Kowollik, Christopher
    ACS MACRO LETTERS, 2016, 5 (05): : 597 - 601
  • [38] Reversible Copper(II)/(I) Electrochemical Potential Switching Driven by Visible Light-Induced Coordinated Ring Rotation
    Nishikawa, Michihiro
    Nomoto, Kuniharu
    Kume, Shoko
    Nishihara, Hiroshi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) : 10543 - 10553
  • [39] Polymer-Fullerene Network Formation via Light-Induced Crosslinking
    Sugawara, Yuuki
    Hiltebrandt, Kai
    Blasco, Eva
    Barner-Kowollik, Christopher
    MACROMOLECULAR RAPID COMMUNICATIONS, 2016, 37 (17) : 1466 - 1471
  • [40] Visible light mediated reductions of ethers, amines and sulfides
    Monos, Timothy M.
    Magallanes, Gabriel
    Sebren, Leanne J.
    Stephenson, Corey R. J.
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2016, 328 : 240 - 248