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原位形成的阳离子钌氢配合物催化的芳基酮与烯烃涉及C-H键活化的区域选择性分子间偶联反应

Regioselective Intermolecular Coupling Reaction of Arylketones and Alkenes Involving C-H Bond Activation Catalyzed by an In-Situ Formed Cationic Ruthenium-Hydride Complex.

作者信息

Yi Chae S, Lee Do W

机构信息

Department of Chemistry, Marquette University, Milwaukee, Wisconsin 53201-1881.

出版信息

Organometallics. 2009 Aug 10;28(15):4266-4268. doi: 10.1021/om900416k.

DOI:10.1021/om900416k
PMID:20161548
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2805103/
Abstract

The cationic ruthenium-hydride complex, formed in-situ from the treatment of the tetranuclear ruthenium-hydride complex {(PCy(3))(CO)RuH(mu(4)-O)(mu(3)-OH)(mu(2)-OH)} with HBF(4).OEt(2), was found to be a highly effective catalyst for the intermolecular coupling reaction of arylketones and 1-alkenes to give the substituted indene and ortho-C-H insertion products. The formation of the indene products was resulted from the initial alkene isomerization followed by regioselective ortho-C-H insertion of 2-alkene and the dehydrative cyclization. The preliminary mechanistic studies revealed a rapid and reversible ortho-C-H bond activation followed by the rate-limiting C-C bond formation step for the coupling reaction.

摘要

由四核氢化钌配合物{(PCy(3))(CO)RuH(μ(4)-O)(μ(3)-OH)(μ(2)-OH)}与HBF(4).OEt(2)原位反应形成的阳离子氢化钌配合物，被发现是芳基酮与1-烯烃分子间偶联反应生成取代茚和邻位C-H插入产物的高效催化剂。茚产物的形成源于最初的烯烃异构化，随后是2-烯烃的区域选择性邻位C-H插入和脱水环化。初步的机理研究表明，该偶联反应存在快速且可逆的邻位C-H键活化，随后是限速的C-C键形成步骤。

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