A new ruthenium-catalyzed hydrogen-transfer reaction: Transformation of 3-benzyl but-1-ynyl ethers into 1,3-dienes and benzaldehyde

被引:51
作者
Yeh, KL [1 ]
Liu, B [1 ]
Lo, CY [1 ]
Huang, HL [1 ]
Liu, RS [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
关键词
D O I
10.1021/ja012623y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equqtion Presentation) We report a ruthenium-catalyzed reaction for various 3-benzyl but-1-ynyl ethers with suitable functionalities. Treatment of these substrates with TpRu(PPh3)(CH3CN)2PF6 (8.0 mol %) catalyst in 1,2-dichloroethane (80 °C, 12 h) afforded functionalized 1,3-dienes and benzyl aldehyde in good yields. This process is considered to be a tandem dealkoxylation and transfer hydrogenation. Deuterium-labeling experiments reveal that the migration of different hydrogen atoms proceeds regiospecifically. A plausible mechanism is proposed on the basis of the results of isotope experiment. Copyright © 2002 American Chemical Society.
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页码:6510 / 6511
页数:2
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