Synthesis of (Z)-1-Aza-1,3-enynes by the Cross-Coupling of Terminal Alkynes with Isocyanides Catalyzed by Rare-Earth Metal Complexes

被引:59
|
作者
Zhang, Wen-Xiong [1 ,2 ,3 ]
Nishiura, Masayoshi [1 ]
Hou, Zhaomin [1 ]
机构
[1] RIKEN, Organomet Chem Lab, Adv Sci Inst, Wako, Saitama 3510198, Japan
[2] Peking Univ, BNLMS, Beijing 100871, Peoples R China
[3] Peking Univ, Coll Chem, Beijing 100871, Peoples R China
基金
日本学术振兴会; 中国国家自然科学基金;
关键词
cross-coupling; enynes; isocyanides; rare-earth metals; sandwich complexes;
D O I
10.1002/anie.200804306
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Rare reactivity: A binuclear catalyst intermediate leads to the Z-selective cross-coupling of terminal alkynes with isocyanides to exclusively yield the (Z)-1-aza-1,3-enyne products for the first time (see scheme). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:9700 / 9703
页数:4
相关论文
共 50 条
  • [41] Stereoselective synthesis of (E)-1,3-enynyl bromides via Pd/Cu-catalyzed cross-coupling reaction of (Z)-α-bromovinylstannanes
    Cai, MZ
    Zhao, H
    CHINESE CHEMICAL LETTERS, 2004, 15 (10) : 1157 - 1160
  • [42] Synthesis and Characterization of N,N,C and N,N,O Tridentate β-Diketiminato Rare-Earth Metal Alkyl Complexes and Their Catalytic Performances on the Dimerization of Aldehydes or Terminal Alkynes
    Zhu, Xiancui
    Wang, Ziqian
    Zha, Ling
    Zhang, Yiwei
    Qi, Yawen
    Yuan, Qingbing
    Zhou, Shuangliu
    Wang, Shaowu
    ORGANOMETALLICS, 2022, 41 (09) : 1087 - 1098
  • [43] Synthesis and characterization of 2-t-butylimino-functionalized indolyl rare-earth metal amido complexes for the catalytic addition of terminal alkynes to carbodiimides: the dimeric complexes with the alkynide species in the μ-η1:η2 bonding modes
    Feng, Zhijun
    Huang, Zeming
    Wang, Shaowu
    Wei, Yun
    Zhou, Shuangliu
    Zhu, Xiancui
    DALTON TRANSACTIONS, 2019, 48 (29) : 11094 - 11102
  • [44] Rare-earth Metal Dialkyl Complexes Supported by 1,3-Disubstituted Indolyl Ligand: Synthesis, Characterization and Catalytic Activity for Isoprene Polymerization
    郭立平
    宋任远
    ChineseJournalofStructuralChemistry, 2021, 40 (08) : 1055 - 1060
  • [45] Neutral and monocationic half-sandwich methyl rare-earth metal complexes: Synthesis, structure, and 1,3-butadiene polymerization catalysis
    Robert, Dominique
    Spaniol, Thomas P.
    Okuda, Jun
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2008, (18) : 2801 - 2809
  • [46] Rare-earth Metal Dialkyl Complexes Supported by 1,3-Disubstituted Indolyl Ligand: Synthesis, Characterization and Catalytic Activity for Isoprene Polymerization
    Guo Li-Ping
    Song Ren-Yuan
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2021, 40 (08) : 1055 - 1060
  • [47] Highly convergent, stereospecific synthesis of 11-cis-retinoids by metal-catalyzed cross-coupling reactions of (Z)-1-alkenylmetals
    Lopez, Susana
    Montenegro, Javier
    Saa, Carlos
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25): : 9572 - 9581
  • [48] A facile stereoselective synthesis of (Z,E)-2-silyl-substituted 1,3-dienes via palladium-catalyzed cross-coupling reaction
    Cai, MZ
    Ye, XL
    Wang, PP
    SYNTHESIS-STUTTGART, 2005, (16): : 2654 - 2656
  • [49] Synthesis of (Z)-tributylstannyl enynes: systematic studies of Sonogashira cross-coupling reactions between (E)-1-iodovinyl-1-tributylstannanes and terminal acetylenes using amines or tetrabutylammonium hydroxide (TBAOH) as activator
    Nazario, Carlos E. D.
    Santana, Amanda S.
    Kawasoko, Cristiane Y.
    Carollo, Carlos A.
    Hurtado, Gabriela R.
    Viana, Luiz H.
    Barbosa, Sandro L.
    Guerrero, Palimecio G., Jr.
    Marques, Francisco A.
    Dabdoub, Vania B.
    Dabdoub, Miguel J.
    Baroni, Adriano C. M.
    TETRAHEDRON LETTERS, 2011, 52 (32) : 4177 - 4181
  • [50] SYNTHESIS OF SYMMETRICAL AND UNSYMMETRIC 1,4-BIS(P-R-PHENYLETHYNYL)BENZENES VIA PALLADIUM COPPER-CATALYZED CROSS-COUPLING AND COMMENTS ON THE COUPLING OF ARYL HALIDES WITH TERMINAL ALKYNES
    NGUYEN, P
    ZHENG, YA
    AGOCS, L
    LESLEY, G
    MARDER, TB
    INORGANICA CHIMICA ACTA, 1994, 220 (1-2) : 289 - 296