炔烃
化学
三键
钌
电泳剂
催化作用
马尔科夫尼科夫法则
还原消去
药物化学
区域选择性
双键
有机化学
作者
Bing Wang,Julong Jiang,Haizhu Yu,Yao Fu
出处
期刊:Organometallics
[American Chemical Society]
日期:2017-01-26
卷期号:36 (3): 523-529
被引量:14
标识
DOI:10.1021/acs.organomet.6b00717
摘要
Vinyl chlorides can be effectively prepared via alkyne hydrochlorination catalyzed by the [Cp*RuCl(cod)]/PPh3 system. The reaction mechanism has been elucidated by density functional theory calculations. Different from the previously proposed pathway (oxidative addition, alkyne coordination, H-/Cl-transfer via inner addition, and reductive elimination), the calculation results indicate that HCl favorably attacks the alkyne stepwise from the outer coordination sphere of the Ru center. The reaction is essentially the electrophilic addition of HCl to alkyne. Therefore, the proton tends to attack the more negatively charged carbon of the C–C triple bond, leading to the Markovnikov product.
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