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
  • [21] A NEW AND CONVENIENT METHOD FOR PREPARATION OF ISOMERICALLY PURE ALPHA,BETA-UNSATURATED DERIVATIVES VIA HYDROALUMINATION OF ALKYNES
    ZWEIFEL, G
    STEELE, RB
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (11) : 2754 - &
  • [22] Copper(I)-Catalysed Deacetylenative Cross-Coupling Reaction of Terminal Alkynes with Propargylic Amines via C(sp)-C(sp3) Bond Cleavage
    Kim, Yongeun
    Nakamura, Hiroyuki
    SYNLETT, 2012, (11) : 1686 - 1690
  • [23] CONVENIENT SYNTHESIS OF SPIRO COMPOUNDS BY THE INSERTION OF ALKYNES INTO THE PD-C BOND OF CYCLOPALLADATED 2-BENZYLPYRIDINE
    MAASSARANI, F
    PFEFFER, M
    LEBORGNE, G
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (06) : 488 - 490
  • [24] Selective C-C bond cleavage of quaternary beta-amino aldehydes and beta-amino ketones by sodium-amide-induced Grob-type fragmentation
    Molm, D
    Risch, N
    LIEBIGS ANNALEN-RECUEIL, 1997, (08): : 1765 - 1767
  • [25] FORMATION OF BETA-C-H AGOSTIC ALKENYLZIRCONOCENE COMPLEXES WITH RESPECT TO ABNORMAL HYDROZIRCONATION OF ALKYNES
    ERKER, G
    ZWETTLER, R
    KRUGER, C
    SCHLUND, R
    HYLAKRYSPIN, I
    GLEITER, R
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 346 (01) : C15 - C18
  • [26] Rhodium-catalyzed intramolecular carbosilylation of alkynes via C(sp3)-Si bond cleavage
    Yang, Qi
    Liu, Liang
    Chi, Yue
    Hao, Wei
    Zhang, Wen-Xiong
    Xi, Zhenfeng
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (05): : 860 - 863
  • [27] Rhodium-catalyzed rapid synthesis of substituted phenols from cyclobutenones and alkynes or alkenes via C-C bond cleavage
    Kondo, Teruyuki
    Niimi, Masatsugu
    Nomura, Masato
    Wada, Kenji
    Mitsudo, Take-aki
    TETRAHEDRON LETTERS, 2007, 48 (16) : 2837 - 2839
  • [28] Rhenium-Catalyzed Regioselective Synthesis of Multisubstituted Pyridines from β-Enamino Ketones and Alkynes via C-C Bond Cleavage
    Yamamoto, Shun-ichi
    Okamoto, Kana
    Murakoso, Makiko
    Kuninobu, Yoichiro
    Takai, Kazuhiko
    ORGANIC LETTERS, 2012, 14 (12) : 3182 - 3185
  • [29] FACILE REDUCTIVE CLEAVAGE OF THE C=O BOND OF ACYL HALIDES AND THE C=N BOND OF NITRILES BY HYDROGEN IN THE PRESENCE OF SULFIDO-BRIDGED MOLYBDENUM COMPLEXES
    COONS, DE
    LAURIE, JCV
    HALTIWANGER, RC
    DUBOIS, MR
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (01) : 283 - 285
  • [30] Cu(II)@Luviset clear as recyclable catalyst for the formation of C-C bond in homo-coupling of terminal alkynes
    Wang, Zheng-Jun
    Wang, Peng-Hui
    Lv, Jing-Jing
    Feng, Jiu-Ju
    Xu, Xinhua
    Wang, Ai-Jun
    Au, Chak-Tong
    Qiu, Renhua
    RSC ADVANCES, 2015, 5 (117) : 96372 - 96376