Highly Regio- and Stereoselective Three-Component Nickel-Catalyzed syn-Hydrocarboxylation of Alkynes with Diethyl Zinc and Carbon Dioxide

被引：186
作者：
Li, Suhua [1 ]
Yuan, Weiming [2 ]
Ma, Shengming [1 ,2 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[2] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 11期
基金：
中国国家自然科学基金;
关键词：
alkynes; carbon dioxide; hydrocarboxylation; inorganic fluoride; nickel; NICKEL(0)-MEDIATED SEQUENTIAL ADDITION; TYROSINE KINASE INHIBITORS; METHYLENE-GAMMA-LACTAMS; UNSATURATED-HYDROCARBONS; ARYLATIVE CARBOXYLATION; ALKENYLBORONIC ESTERS; CYTOTOXIC EVALUATION; ORGANOZINC REAGENTS; ALLYL STANNANES; CO2;
D O I：
10.1002/anie.201007128
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Hydrocarboxylation of alkynes: The first example of nickel-catalyzed hydrozincation of alkynes that form stereodefined hydrocarboxylation products is presented (see scheme; cod=cycloocta-1,5-diene). This catalytic system is efficient for the activation of CO2 and the three-component reaction produces products that could be converted into important oxindole or γ-butyrolactam derivatives. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：2578 / 2582
页数：5
相关论文
共 59 条
  • [1] A convenient synthesis and cytotoxic evaluation of β-aryl-α-methylidene-γ-lactones and β-aryl-α-methylidene-γ-lactams
    Albrecht, Anna
    Albrecht, Lukasz
    Rozalski, Marek
    Krajewska, Urszula
    Janecka, Anna
    Studzian, Kazimierz
    Janecki, Tomasz
    [J]. NEW JOURNAL OF CHEMISTRY, 2010, 34 (04) : 750 - 761
  • [2] Antitumor activity of substituted E-3-(3,4,5-trimethoxybenzylidene)-1,3-dihydroindol-2-ones
    Andreani, Aldo
    Burnelli, Silvia
    Granaiola, Massimiliano
    Leoni, Alberto
    Locatelli, Alessandra
    Morigi, Rita
    Rambaldi, Mirella
    Varoli, Lucilla
    Kunkel, Mark W.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (23) : 6922 - 6924
  • [3] Bidentate amidine ligands for nickel(0)-mediated coupling of carbon dioxide with unsaturated hydrocarbons
    Aoki, M
    Kaneko, M
    Izumi, S
    Ukai, K
    Iwasawa, N
    [J]. CHEMICAL COMMUNICATIONS, 2004, (22) : 2568 - 2569
  • [4] Ni(0)-promoted hydroxycarboxylation of 1,2-dienes by reaction with CO2 and O2
    Aoki, Masao
    Izumi, Sawa
    Kaneko, Motomu
    Ukai, Kazutoshi
    Takaya, Jun
    Iwasawa, Nobuharu
    [J]. ORGANIC LETTERS, 2007, 9 (07) : 1251 - 1253
  • [5] NEW NICKEL-CARBON DIOXIDE COMPLEX - SYNTHESIS, PROPERTIES, AND CRYSTALLOGRAPHIC CHARACTERIZATION OF (CARBON DIOXIDE)-BIS(TRICYCLOHEXYLPHOSPHINE)NICKEL
    ARESTA, M
    NOBILE, CF
    ALBANO, VG
    FORNI, E
    MANASSERO, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (15) : 636 - 637
  • [6] Utilisation of CO2 as a chemical feedstock:: opportunities and challenges
    Aresta, Michele
    Dibenedetto, Angela
    [J]. DALTON TRANSACTIONS, 2007, (28) : 2975 - 2992
  • [7] STUDY OF HALOGEN CARBON-DIOXIDE CLUSTERS AND THE FLUOROFORMYLOXYL RADICAL BY PHOTODETACHMENT OF X(-)(CO2) (X=I,CL,BR) AND FCO2-
    ARNOLD, DW
    BRADFORTH, SE
    KIM, EH
    NEUMARK, DM
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1995, 102 (09) : 3493 - 3509
  • [8] SYNTHESIS OF POTENTIAL CYTOTOXIC ALPHA-METHYLENE GAMMA-LACTAMS
    BELAUD, C
    ROUSSAKIS, C
    LETOURNEUX, Y
    ELALAMI, N
    VILLIERAS, J
    [J]. SYNTHETIC COMMUNICATIONS, 1985, 15 (14) : 1233 - 1243
  • [9] Correa A., 2009, ANGEW CHEM, V121, P6317
  • [10] Palladium-Catalyzed Direct Carboxylation of Aryl Bromides with Carbon Dioxide
    Correa, Arkaitz
    Martin, Ruben
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (44) : 15974 - +
123456