期刊
JOURNAL OF ORGANOMETALLIC CHEMISTRY
卷 689, 期 23, 页码 3820-3830出版社
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2004.07.025
关键词
water-soluble ligand; boronic acids; homogeneous biphasic catalysis; rhodium; arylation of alkynes
The versatile preparation of trisubstituted alkenes via selective Rh-catalyzed arylation of alkynes is described in water and in a water/toluene biphasic system. For hydrophobic alkyl alkynes, the reaction afforded either alkenes or dienes depending on the temperature and the solvent conditions. Aryl, heteroaryl, silylated and alkyl substituted alkynes reacted equally well with various boronic acids, leading regioselectively to functionalized alkenyl derivatives in high yields (65-99%). The mechanism was investigated in toluene/water mixture or water and involves a vinylrhodium complex. The efficient recycling of the Rh/m-TPPTC system is disclosed with excellent yield (92-96%) and purity of the alkene. (C) 2004 Elsevier B.V. All rights reserved.
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