A new approach to access difluoroalkylated diarylmethanes via visible-light photocatalytic cross-coupling reactions

被引:69
|
作者
Zhao, Yin-Na [1 ]
Luo, Yong-Chun [1 ]
Wang, Zhu-Yin [1 ]
Xu, Peng-Fei [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
关键词
PARA-QUINONE METHIDES; ARYL BORONIC ACIDS; ASYMMETRIC 1,6-CONJUGATE ADDITION; PHOTOREDOX CATALYSIS; ALPHA-ALKYLATION; EXPEDIENT ACCESS; PALLADIUM; RADICALS; ALDEHYDES; ARENES;
D O I
10.1039/c8cc01486h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Difluoroalkylated diarylmethanes with biological and pharmacological potentials were synthesized from para-quinone methides (p-QMs) and difluoroalkylating reagents via a visible light photocatalysis strategy. Mechanism studies showed that the excited photocatalyst, *fac-Ir(ppy)(3), was primarily quenched by p-QMs and the generated diarylmethane radical intermediates then underwent a radical-radical cross-coupling reaction with difluoroalkyl radicals. This reaction features mild conditions, high efficiency and wide functional group compatibility.
引用
收藏
页码:3993 / 3996
页数:4
相关论文
共 50 条
  • [21] Visible-light induced cross-electrophile coupling of imines and anhydrides to synthesize α-amino ketones
    Cao, Renxu
    Liu, Yu
    Shi, Xiaoxin
    Zheng, Jun
    CHEMICAL COMMUNICATIONS, 2023, 59 (71) : 10668 - 10671
  • [22] Brønsted Acid-Facilitated Thioetherification Cross-Coupling Reactions with Nickel and Visible Light
    Nikitin, Maksim
    Otvos, Sandor B.
    Ghosh, Indrajit
    Philipp, Maximilian
    Gschwind, Ruth
    Kappe, C. Oliver
    Konig, Burkhard
    ACS CATALYSIS, 2025,
  • [23] The recent achievements of redox-neutral radical C-C cross-coupling enabled by visible-light
    Xie, Jin
    Jin, Hongming
    Hashmi, A. Stephen K.
    CHEMICAL SOCIETY REVIEWS, 2017, 46 (17) : 5193 - 5203
  • [24] Asymmetric Radical-Radical Cross-Coupling through Visible-Light-Activated Iridium Catalysis
    Wang, Chuanyong
    Qin, Jie
    Shen, Xiaodong
    Riedel, Radostan
    Harms, Klaus
    Meggers, Eric
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (02) : 685 - 688
  • [25] Recent Advances in Transition Metal-Catalyzed Cross-Coupling Reactions Directly Promoted by Visible Light
    Li, Zhenlong
    Jin, Jian
    Huang, Shahua
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (03) : 563 - 574
  • [26] Synthesis of functionalized diarylmethanes via a copper-catalyzed cross-coupling of arylmagnesium reagents with benzylic phosphates
    Kofink, Christiane C.
    Knochel, Paul
    ORGANIC LETTERS, 2006, 8 (18) : 4121 - 4124
  • [27] Visible Light-Promoted Oxidative Cross-Coupling of Alcohols to Esters
    Dellisanti, Andrea
    Chessa, Elisa
    Porcheddu, Andrea
    Carraro, Massimo
    Pisano, Luisa
    De Luca, Lidia
    Gaspa, Silvia
    MOLECULES, 2024, 29 (03):
  • [28] A Cascade Cross-Coupling and in Situ Hydrogenation Reaction by Visible Light Catalysis
    Zhong, Jian-Ji
    Wu, Cheng-Juan
    Meng, Qing-Yuan
    Gao, Xue-Wang
    Lei, Tao
    Tung, Chen-Ho
    Wu, Li-Zhu
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (13) : 2846 - 2852
  • [29] A Cascade Cross-Coupling Hydrogen Evolution Reaction by Visible Light Catalysis
    Meng, Qing-Yuan
    Zhong, Jian-Ji
    Liu, Qiang
    Gao, Xue-Wang
    Zhang, Hui-Hui
    Lei, Tao
    Li, Zhi-Jun
    Feng, Ke
    Chen, Bin
    Tung, Chen-Ho
    Wu, Li-Zhu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (51) : 19052 - 19055
  • [30] Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex
    Pan, Pan
    Liu, Shihan
    Lan, Yu
    Zeng, Huiying
    Li, Chao-Jun
    CHEMICAL SCIENCE, 2022, 13 (24) : 7165 - 7171