A new ruthenium-catalyzed hydrogen-transfer reaction: transformation of 3-benzyl but-1-ynyl ethers into 1,3-dienes and benzaldehyde.
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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一种新的钌催化氢转移反应：3-苄基丁-1-炔基醚转化为1,3-二烯和苯甲醛。
DOI：
10.1021/ja012623y
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发表时间：
2002
影响因子：
15
通讯作者：
Rai‐Shung Liu
中科院分区：
文献类型：
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作者：
K. Yeh;Bo Liu;C. Lo;Heh;Rai‐Shung Liu
我们报道了一种具有合适官能度的3-苄基丁-1-炔基醚的合成反应。用TpRu（PPh3）（CH3CN）2PF6（8.0摩尔%）催化剂在1，2-二氯乙烷中处理这些底物（80 ℃，12小时），以良好的产率得到官能化的1，3-二烯和苯甲醛。该方法被认为是串联脱烷氧基化和转移氢化。氘标记实验表明，不同的氢原子的迁移进行区域特异性。根据同位素实验结果提出了可能的机理。
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.