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

Kuo-Liang Yeh; Bo Liu; Ching-Yu Lo; Heh-Lung Huang; Rai-Shung Liu

doi:10.1021/ja012623y

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

J Am Chem Soc. 2002 Jun 12;124(23):6510-1. doi: 10.1021/ja012623y.

Authors

Kuo-Liang Yeh¹, Bo Liu, Ching-Yu Lo, Heh-Lung Huang, Rai-Shung Liu

Affiliation

¹ Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC.

PMID: 12047152
DOI: 10.1021/ja012623y

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.