Abstract
(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(PPh 3 )(CH 3 CN) 2 PF 6 (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.