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配体和底物对区域和立体选择性Ru(II)催化的乙烯基酯氢酰氧基化反应的影响。

Ligand and Substrate Effects on Regio- and Stereoselective Ru(II)-Catalyzed Hydroacyloxylations to Vinylic Esters.

作者信息

Beasley Paul A, McDonald Frank E

机构信息

Department of Chemistry, Emory University, Atlanta, Georgia 30322, United States of America.

出版信息

Adv Synth Catal. 2024 Feb 20;366(4):1013-1018. doi: 10.1002/adsc.202301222. Epub 2024 Jan 9.

DOI:10.1002/adsc.202301222
PMID:40855865
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12377056/
Abstract

Two Ru(II)-catalytic systems were developed for anti-Markovnikov regioselective hydroacyloxylations of terminal alkynes to vinylic esters. [Ru(NCCH)][(BF)] favors ()-vinylic ester products with arylacetylenes and select carboxylic acids, whereas a Ru scorpionate complex with two electron-withdrawing ligands favors ()-vinylic ester isomers.

摘要

开发了两种钌(II)催化体系,用于将末端炔烃进行反马氏区域选择性氢酰氧基化反应生成乙烯基酯。[Ru(NCCH)][(BF)]有利于芳基乙炔与特定羧酸生成()-乙烯基酯产物,而带有两个吸电子配体的钌(II)螯合物有利于生成()-乙烯基酯异构体。

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本文引用的文献

1
Transition Metal Vinylidene- and Allenylidene-Mediated Catalysis in Organic Synthesis.过渡金属亚乙烯基和烯丙基介导的有机合成催化反应。
Chem Rev. 2019 Mar 27;119(6):4293-4356. doi: 10.1021/acs.chemrev.8b00568. Epub 2019 Feb 15.
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Enol Ester Synthesis via Cobalt-Catalyzed Regio- and Stereoselective Addition of Carboxylic Acids to Alkynes.通过钴催化的羧酸对炔烃的区域和立体选择性加成反应合成烯醇酯。
Org Lett. 2018 Nov 2;20(21):6719-6724. doi: 10.1021/acs.orglett.8b02824. Epub 2018 Oct 25.
3
Regioselective Formation of Enol Esters from the Ruthenium-Catalyzed Markovnikov Addition of Carboxylic Acids to Alkynes.钌催化羧酸对炔烃的马氏加成反应区域选择性地形成烯醇酯。
J Org Chem. 2016 Jan 15;81(2):476-84. doi: 10.1021/acs.joc.5b02293. Epub 2016 Jan 4.
4
Broad-spectrum catalysts for the ambient temperature anti-Markovnikov hydration of alkynes.用于炔烃在环境温度下反马氏加成水合的广谱催化剂。
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Scorpionates bearing nitro substituents: mono-, bis- and tris-(3-nitro-pyrazol-1-yl)borate ligands and their copper(I) complexes.含硝基取代基的硼酸盐:单、双和三-(3-硝基-吡唑-1-基)硼酸酯配体及其铜(I)配合物。
Dalton Trans. 2010 Oct 14;39(38):8937-44. doi: 10.1039/c0dt00474j. Epub 2010 Aug 16.
8
Scope and Mechanistic Investigations on the Solvent-Controlled Regio- and Stereoselective Formation of Enol Esters from the Ruthenium-Catalyzed Coupling Reaction of Terminal Alkynes and Carboxylic Acids.钌催化末端炔烃与羧酸的偶联反应中溶剂控制烯醇酯区域和立体选择性形成的范围及机理研究
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