Pd-Catalyzed Transfer of Difluorocarbene

被引:107
|
作者
Deng, Xiao-Yun [1 ]
Lin, Jin-Hong [1 ]
Xiao, Ji-Chang [1 ]
机构
[1] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
关键词
COPPER-MEDIATED DIFLUOROMETHYLATION; C-F BONDS; DIAZO-COMPOUNDS; COMPLEXES; TRIFLUOROMETHYLATION; IODIDES; ARYL; TETRAFLUOROETHYLENE; PHOSPHABETAINE; METATHESIS;
D O I
10.1021/acs.orglett.6b02141
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The study of transition-metal difluorocarbene complex has long been a subject of active investigation, but the transition-metal-catalyzed transfer of difluorocarbene remains a significant challenge. The Pd-catalyzed transfer of difluorocarbene is described to realize the coupling reaction of boronic acids with difluorocarbene to give (difluoromethyl)arenes and -olefins. Mechanistic investigations reveal that the Pd=CF2 complex is an important intermediate for this transformation. This complex is prone to trimerization without the presence of starting materials.
引用
收藏
页码:4384 / 4387
页数:4
相关论文
共 50 条
  • [1] Pd-Catalyzed Transfer of Difluorocarbene for Three Component Cross-Coupling
    Xu, Zhi-Wei
    Zhang, Wei
    Lin, Jin-Hong
    Jin, Chuan-Ming
    Xiao, Ji-Chang
    CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (12) : 1647 - 1650
  • [2] Pd-Catalyzed Synthesis of Aryl Esters Involving Difluorocarbene Transfer Carbonylation
    Wang, Lu
    Hu, Chengxian
    Yang, Xue
    Fu, Ying
    Du, Zhengyin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (10)
  • [3] Access to Difluoromethylated Arenes by Pd-Catalyzed Reaction of Arylboronic Acids with Bromodifluoroacetate
    Feng, Zhang
    Min, Qiao-Qiao
    Zhang, Xingang
    ORGANIC LETTERS, 2016, 18 (01) : 44 - 47
  • [4] Polymer-Supported Siloxane Transfer Agents for Pd-Catalyzed Cross-Coupling Reactions
    Nguyen, Minh H.
    Smith, Amos B., III
    ORGANIC LETTERS, 2013, 15 (16) : 4258 - 4261
  • [5] Reductive Catalytic Difluorocarbene Transfer via Palladium Catalysis
    Zhang, Xue-Ying
    Sun, Shi-Ping
    Sang, Yue-Qian
    Xue, Xiao-Song
    Min, Qiao-Qiao
    Zhang, Xingang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (37)
  • [6] Pd-Catalyzed Stereoselective Carboperfluoroalkylation of Alkynes
    Li, Zhaodong
    Garcia-Dominguez, Andres
    Nevado, Cristina
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (36) : 11610 - 11613
  • [7] Pd-Catalyzed Regioselective Arylboration of Vinylarenes
    Yang, Kai
    Song, Qiuling
    ORGANIC LETTERS, 2016, 18 (21) : 5460 - 5463
  • [8] Pd-Catalyzed Carbonylation of Acyl Azides
    Li, Zongyang
    Xu, Shiyang
    Huang, Baoliang
    Yuan, Chenhui
    Chang, Wenxu
    Fu, Bin
    Jiao, Lei
    Wang, Peng
    Zhang, Zhenhua
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (15) : 9497 - 9508
  • [9] Pd-Catalyzed Difluoromethylation of Vinyl Bromides, Triflates, Tosylates, and Nonaflates
    Chang, Dalu
    Gu, Yang
    Shen, Qilong
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (16) : 6074 - 6078
  • [10] Controllable catalytic difluorocarbene transfer enables access to diversified fluoroalkylated arenes
    Fu, Xia-Ping
    Xue, Xiao-Song
    Zhang, Xue-Ying
    Xiao, Yu-Lan
    Zhang, Shu
    Guo, Yin-Long
    Leng, Xuebing
    Houk, Kendall N.
    Zhang, Xingang
    NATURE CHEMISTRY, 2019, 11 (10) : 948 - 956