A new ruthenium-catalyzed hydrogen-transfer reaction: transformation of 3-benzyl but-1-ynyl ethers into 1,3-dienes and benzaldehyde |
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Authors: | Yeh Kuo-Liang Liu Bo Lo Ching-Yu Huang Heh-Lung Liu Rai-Shung |
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Institution: | Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC. |
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Abstract: | 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 degrees 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. |
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