Visible-light-driven nickel-catalyzed reductive cross-coupling of benzyltrimethylammonium triflates with aryl bromides

被引:0
|
作者
Tian, Ren-Gui
Yu, Mengyao
Ni, Bo
Zhang, Muliang [1 ]
Tian, Shi-Kai [1 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Res Ctr Phys Sci Microscale, Key Lab Precis & Intelligent Chem, Hefei 230026, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
C-N BOND; AMMONIUM-SALTS; TRANSFORMATIONS; CLEAVAGE;
D O I
10.1039/d5ob00215j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diarylmethanes are significant molecules in organic synthesis and play a vital role in pharmaceutical development. In this context, we successfully developed a visible-light-driven nickel-catalyzed cross-coupling of readily available benzyltrimethylammonium triflates with aryl bromides, enabling the direct synthesis of various diarylmethane products without the need for metal-reducing agents. Mechanistic studies have revealed that benzyl radicals, generated through photocatalysis, may serve as key intermediates, offering a novel approach to the reductive coupling of organic quaternary ammonium salts.
引用
收藏
页数:4
相关论文
共 50 条
  • [31] Nickel-catalyzed cross-coupling of aryltrimethylammonium triflates and amines
    Zhang, Xue-Qi
    Wang, Zhong-Xia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (09) : 1448 - 1453
  • [32] Nickel-catalyzed Reductive Cross-Coupling Reaction
    Sakamoto, Ryu
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2015, 73 (06) : 649 - 650
  • [33] Nickel-catalyzed direct cross-coupling of heterocyclic phosphonium salts with aryl bromides
    Cui, Yan-Ying
    Li, Wen-Xin
    Ma, Na-Na
    Shen, Chuanji
    Zhou, Xiaocong
    Chu, Xue-Qiang
    Rao, Weidong
    Shen, Zhi-Liang
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (24) : 6931 - 6936
  • [34] Paired electrolysis-enabled nickel-catalyzed enantioselective reductive cross-coupling between α-chloroesters and aryl bromides
    Dong Liu
    Zhao-Ran Liu
    Zhen-Hua Wang
    Cong Ma
    Simon Herbert
    Hartmut Schirok
    Tian-Sheng Mei
    Nature Communications, 13
  • [35] Paired electrolysis-enabled nickel-catalyzed enantioselective reductive cross-coupling between α-chloroesters and aryl bromides
    Liu, Dong
    Liu, Zhao-Ran
    Wang, Zhen-Hua
    Ma, Cong
    Herbert, Simon
    Schirok, Hartmut
    Mei, Tian-Sheng
    NATURE COMMUNICATIONS, 2022, 13 (01)
  • [36] Palladium- or nickel-catalyzed cross-coupling of organotitanium reagents with aryl triflates and halides
    Han, JW
    Tokunaga, N
    Hayashi, T
    SYNLETT, 2002, (06) : 871 - 874
  • [37] Nickel-Catalyzed Reductive Three-Component Cross-Coupling of Butadiene with Aldehydes and Alkenyl Triflates/Bromides: Access to Skipped Dienes
    Xu, Yan
    Su, Tong
    Zhang, Jie-Rui
    Ding, Hua-Jiao
    Gao, Yuanji
    Xu, Minghui
    Cao, Peng
    Hu, Ping
    Wang, Bi-Qin
    Chen, Bin
    ORGANIC LETTERS, 2023, 25 (17) : 3136 - 3140
  • [38] Nickel-Catalyzed Reductive Cross-Coupling of Benzylic Sulfonium Salts with Aryl Iodides
    Wang, Wei
    Yao, Ken
    Wu, Fan
    SYNLETT, 2022, 33 (04) : 361 - 366
  • [39] Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides
    DeLano, Travis J.
    Dibrell, Sara E.
    Lacker, Caitlin R.
    Pancoast, Adam R.
    Poremba, Kelsey E.
    Cleary, Leah
    Sigman, Matthew S.
    Reisman, Sarah E.
    CHEMICAL SCIENCE, 2021, 12 (22) : 7758 - 7762
  • [40] Nickel-Catalyzed Reductive Coupling of Aryl Bromides with Tertiary Alkyl Halides
    Wang, Xuan
    Wang, Shan
    Xue, Weichao
    Gong, Hegui
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (36) : 11562 - 11565