FACILE CLEAVAGE OF THE C-BETA-C-BETA'-BOND OF ZIRCONACYCLOPENTENES - CONVENIENT METHOD FOR SELECTIVELY COUPLING ALKYNES WITH ALKYNES, NITRILES, AND ALDEHYDES

被引:193
|
作者
TAKAHASHI, T [1 ]
KAGEYAMA, M [1 ]
DENISOV, V [1 ]
HARA, R [1 ]
NEGISHI, E [1 ]
机构
[1] PURDUE UNIV,DEPT CHEM,W LAFAYETTE,IN 47907
关键词
D O I
10.1016/S0040-4039(00)61653-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of zirconacyclopentenes (1) with alkynes, nitriles, and aldehydes proceeds via cleavage of the C(beta)-C(beta') bond of 1 and displacement of ethylene by the donors to give the corresponding five-membered zirconacycles, providing a convenient means of selectively coupling alkynes with pi-donor compounds.
引用
收藏
页码:687 / 690
页数:4
相关论文
共 50 条
  • [41] Iodine-catalyzed synthesis of benzoxazoles using catechols, ammonium acetate, and alkenes/alkynes/ketones via C-C and C-O bond cleavage
    Aboonajmi, Jasem
    Panahi, Farhad
    Hosseini, Mina Aali
    Aberi, Mahdi
    Sharghi, Hashem
    RSC ADVANCES, 2022, 12 (32) : 20968 - 20972
  • [42] Palladium-Catalyzed Intermolecular Decarboxylative Coupling of 2-Phenylbenzoic Acids with Alkynes via C-H and C-C Bond Activation
    Wang, Congyang
    Rakshit, Souvik
    Glorius, Frank
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (40) : 14006 - 14008
  • [43] Facile Cu-free Sonogashira cross-coupling of nucleoside C-6 arylsulfonates with terminal alkynes
    Ngassa, Felix N.
    Gomez, Jamie M.
    Haines, Brandon E.
    Ostach, Michael J.
    Hector, Jared W.
    Hoogenboom, Lindsay J.
    Page, Chelsea E.
    TETRAHEDRON, 2010, 66 (40) : 7919 - 7926
  • [44] Rhodium-Catalyzed Addition Cyclization of Hydrazines with Alkynes: Pyrazole Synthesis via Unexpected C-N Bond Cleavage
    Li, Deng Yuan
    Mao, Xiao Feng
    Chen, Hao Jie
    Chen, Guo Rong
    Liu, Pei Nian
    ORGANIC LETTERS, 2014, 16 (13) : 3476 - 3479
  • [45] SI-C BOND-CLEAVAGE IN SILYL ALKYNES UNDER PHASE-TRANSFER CATALYSIS - APPLICATIONS TO THE SYNTHESIS OF EPOXYHEXENYNES
    ROSER, J
    EBERBACH, W
    SYNTHETIC COMMUNICATIONS, 1986, 16 (09) : 983 - 996
  • [46] Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C-CN Bond Cleavage and Cyano Transfer
    Chen, Hui
    Sun, Shuhao
    Liu, Yahu A.
    Liao, Xuebin
    ACS CATALYSIS, 2020, 10 (02) : 1397 - 1405
  • [47] An asymmetric [3+2] cycloaddition of alkynes with oxiranes by selective C-C bond cleavage of epoxides: highly efficient synthesis of chiral furan derivatives
    Chen, Weiliang
    Fu, Xuan
    Lin, Lili
    Yuan, Xiao
    Luo, Weiwei
    Feng, Juhua
    Liu, Xiaohua
    Feng, Xiaoming
    CHEMICAL COMMUNICATIONS, 2014, 50 (78) : 11480 - 11483
  • [48] C-C bond fission via sulphones: A new ring cleavage of cyclic beta-keto phenylsulphones
    Ballini, R
    Bosica, G
    Mecozzi, T
    TETRAHEDRON, 1997, 53 (21) : 7341 - 7346
  • [49] Rhodium(III)-Catalyzed Oxidative Coupling of N-Phenylindole-3-carboxylic Acids with Alkenes and Alkynes via C4-H and C2-H/C2'-H Bond Cleavage
    Okada, Takeshi
    Sakai, Asumi
    Hinoue, Tomoaki
    Satoh, Tetsuya
    Hayashi, Yoshihiro
    Kawauchi, Susumu
    Chandrababunaidu, Kona
    Miura, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (10): : 5639 - 5649
  • [50] Iminophosphorane-based nucleophilic ruthenium(II) carbene complexes:: Unusual C-C coupling and C-H activation promoted by the addition of alkynes to the Ru=C bond
    Cadierno, V
    Díez, J
    García-Alvarez, J
    Gimeno, J
    ORGANOMETALLICS, 2005, 24 (11) : 2801 - 2810