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通过钌催化吡咯与末端炔烃的偶联反应,涉及 C-H 键活化,区域选择性地形成 α-乙烯基吡咯。

Regioselective formation of alpha-vinylpyrroles from the ruthenium-catalyzed coupling reaction of pyrroles and terminal alkynes involving C-H bond activation.

机构信息

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

出版信息

J Org Chem. 2010 May 7;75(9):3144-6. doi: 10.1021/jo100269y.

Abstract

The cationic ruthenium catalyst Ru(3)(CO)(12)/NH(4)PF(6) was found to be highly effective for the intermolecular coupling reaction of pyrroles and terminal alkynes to give gem-selective alpha-vinylpyrroles. The carbon isotope effect on the alpha-pyrrole carbon and the Hammett correlation from a series of para-substituted N-arylpyrroles (rho = -0.90) indicate a rate-limiting C-C bond formation step of the coupling reaction.

摘要

研究发现,阳离子钌催化剂 Ru(3)(CO)(12)/NH(4)PF(6) 对于吡咯和末端炔烃的分子间偶联反应非常有效,可生成高立体选择性的α-乙烯基吡咯。α-吡咯碳的碳同位素效应和一系列对取代 N-芳基吡咯的哈米特相关性(rho = -0.90)表明,该偶联反应的速率限制步骤是 C-C 键形成。

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本文引用的文献

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