Visible Light-Induced Selective Generation of Radicals from Organoborates by Photoredox Catalysis

被引：202
|
作者：
Yasu, Yusuke [1 ]
Koike, Takashi [1 ]
Akita, Munetaka [1 ]
机构：
[1] Tokyo Inst Technol, Chem Resources Lab, Midori Ku, Yokohama, Kanagawa 2268503, Japan
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 18期
关键词：
borates; green chemistry; photooxidation; photoredox catalysis; radical reactions; ARYLBORONIC ACIDS; ELECTRON-TRANSFER; HIGHLY EFFICIENT; OXIDATION; PHOTOCATALYSIS; BONDS; PHOTOCHEMISTRY; CYCLOADDITION; PERSPECTIVES; STRATEGY;
D O I：
10.1002/adsc.201200588
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A new strategy for the generation of carbon-centered radicals via oxidation of alkyl-, allyl-, benzyl- and arylborates by visible-light-driven single electron transfer (SET) photoredox catalysis has been established. The generated radicals smoothly react with TEMPO and electron-deficient alkenes to afford C?O and C?C coupling products, respectively. In this radical initiating system, cyclic organo(triol)borates turn out to be useful radical precursors.
引用
收藏
页码：3414 / 3420
页数：7
相关论文
共 50 条
  • [1] Accelerating radicals generation by photoredox catalysis from organoborates in continuous microflow reactor
    El Achi, Nassim
    Penhoat, Mael
    Rolando, Christian
    Chausset-Boissarie, Laetitia
    19TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY, 2015,
  • [2] Generation and Application of Iminyl Radicals from Oxime Derivatives Enabled by Visible Light Photoredox Catalysis
    Song, Changhua
    Shen, Xu
    Yu, Fang
    He, Yupeng
    Yu, Shouyun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (11) : 3748 - 3759
  • [3] A Desulfurative Strategy for the Generation of Alkyl Radicals Enabled by Visible-Light Photoredox Catalysis
    Xue, Fei
    Wang, Falu
    Liu, Jiazhen
    Di, Jiamei
    Liao, Qi
    Lu, Huifang
    Zhu, Min
    He, Liping
    He, Huan
    Zhang, Dan
    Song, Hao
    Liu, Xiao-Yu
    Qin, Yong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (22) : 6667 - 6671
  • [4] Benign perfluoroalkylation of uracils and uracil nucleosides via visible light-induced photoredox catalysis
    Zhang, Ben-Hou
    Kong, Jing-Jing
    Huang, Yang
    Lou, Yue-Guang
    Li, Xiao-Fei
    He, Chun-Yang
    CHINESE CHEMICAL LETTERS, 2017, 28 (08) : 1751 - 1754
  • [5] Asymmetric synthesis of chiral imidazolidines by merging copper and visible light-induced photoredox catalysis
    Dai, Linlong
    Zhu, Qiaohong
    Zeng, Jie
    Liu, Yuheng
    Zhong, Guofu
    Han, Xiaoyu
    Zeng, Xiaofei
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (11) : 2994 - 2999
  • [6] Benign perfluoroalkylation of uracils and uracil nucleosides via visible light-induced photoredox catalysis
    Ben-Hou Zhang
    Jing-Jing Kong
    Yang Huang
    Yue-Guang Lou
    Xiao-Fei Li
    Chun-Yang He
    ChineseChemicalLetters, 2017, 28 (08) : 1751 - 1754
  • [7] Photoredox Catalysis with Visible Light
    Zeitler, Kirsten
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9785 - 9789
  • [8] Selective difluoroalkylation of alkenes by using visible light photoredox catalysis
    Yu, Chunghyeon
    Iqbal, Naeem
    Park, Sehyun
    Cho, Eun Jin
    CHEMICAL COMMUNICATIONS, 2014, 50 (85) : 12884 - 12887
  • [9] Acyl Radicals from Aromatic Carboxylic Acids by Means of Visible-Light Photoredox Catalysis
    Bergonzini, Giulia
    Cassani, Carlo
    Wallentin, Carl-Johan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) : 14066 - 14069
  • [10] Carbonylation of Alkyl Radicals Derived from Organosilicates through Visible-Light Photoredox Catalysis
    Cartier, Alex
    Levernier, Etienne
    Corce, Vincent
    Fukuyama, Takahide
    Dhimane, Anne-Lise
    Ollivier, Cyril
    Ryu, Ilhyong
    Fensterbank, Louis
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (06) : 1789 - 1793
12345