Palladium-catalyzed chloroimination of imidoyl chlorides to a triple bond: An intramolecular reaction leading to 4-chloroquinolines

被引:48
作者
Isobe, Akira [1 ]
Takagi, Jun [1 ]
Katagiri, Toshimasa [1 ]
Uneyama, Kenji [1 ]
机构
[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan
关键词
D O I
10.1021/ol800512m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this paper, a new type of effective chloroimination was reported. This reaction afforded 4-chloro-2-perfluoroalkyl quinolines from fluorinated imidoyl chlorides in high yields. This is the first achievement of oxidative addition-reductive elimination type C-Cl bond activation by chloropalladation.
引用
收藏
页码:2657 / 2659
页数:3
相关论文
共 50 条
  • [41] Palladium-Catalyzed Desulfitative Cross-Coupling Reaction of Sodium Sulfinates with Benzyl Chlorides
    Zhao, Feng
    Tan, Qi
    Xiao, Fuhong
    Zhang, Shufeng
    Deng, Guo-Jun
    ORGANIC LETTERS, 2013, 15 (07) : 1520 - 1523
  • [42] A General Palladium-Catalyzed Hiyama Cross-Coupling Reaction of Aryl and Heteroaryl Chlorides
    Yuen, On Ying
    So, Chau Ming
    Man, Ho Wing
    Kwong, Fuk Yee
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (19) : 6471 - 6476
  • [43] PALLADIUM-CATALYZED SEQUENTIAL BOND FORMATION LEADING TO CONJUGATED ENE-YNE SYSTEM
    TORII, S
    OKUMOTO, H
    TADOKORO, T
    NISHIMURA, A
    RASHID, MA
    TETRAHEDRON LETTERS, 1993, 34 (13) : 2139 - 2142
  • [44] Palladium-catalyzed cross-coupling reaction of organobismuth compounds with aryl and alkenyl chlorides
    Yamazaki, O
    Tanaka, T
    Shimada, S
    Suzuki, Y
    Tanaka, M
    SYNLETT, 2004, (11) : 1921 - 1924
  • [45] Efficient Synthesis of Imidazole-Fused Benzodiazepines Using Palladium-Catalyzed Intramolecular C-N Bond Formation Reaction
    Mitra, Sudipta
    Darira, Heena
    Chattopadhyay, Partha
    SYNTHESIS-STUTTGART, 2013, 45 (01): : 85 - 92
  • [46] Palladium-Catalyzed C-C Bond Activation/Suzuki Reaction of Methylenecyclobutanes
    Chen, Xiao-Bing
    Li, Li
    Yang, Wan-Chun
    Song, Kun-Long
    Wu, Bin
    Gan, Wan-Er
    Cao, Jian
    Xu, Li-Wen
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (06) : 1611 - 1615
  • [47] A highly efficient heterogeneous palladium-catalyzed cascade three-component reaction of acid chlorides, terminal alkynes and hydrazines leading to pyrazoles
    Chen, Qiurong
    Yao, Fang
    Yin, Lin
    Cai, Mingzhong
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2016, 804 : 108 - 113
  • [48] Palladium-catalyzed intramolecular C-O bond formation: An approach to the synthesis of chiral benzodioxocines
    Neogi, Arpita
    Majhi, Tirtha P.
    Achari, Basudeb
    Chattopadhyay, Partha
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (02) : 330 - 336
  • [49] Palladium-Catalyzed Synthesis of Phenanthridine/Benzoxazine-Fused Quinazolinones by Intramolecular CH Bond Activation
    Gupta, Puneet K.
    Yadav, Nisha
    Jaiswal, Subodh
    Asad, Mohd.
    Kant, Ruchir
    Hajela, Kanchan
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (38) : 13210 - 13215
  • [50] Palladium-Catalyzed Intramolecular Cyclization of Ynamides: Synthesis of 4-Halo-oxazolones
    Huang, Hai
    He, Guangke
    Zhu, Guohao
    Zhu, Xiaolin
    Qiu, Shineng
    Zhu, Hongjun
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (07) : 3480 - 3487