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N-杂环卡宾(NHC)-金/银/铜苯并三唑基配合物的合成及其在炔丙酰胺环异构化和羰基硅氢化反应中的催化活性。

Synthesis of N-heterocyclic carbene (NHC)-Au/Ag/Cu benzotriazolyl complexes and their catalytic activity in propargylamide cycloisomerization and carbonyl hydrosilylation reactions.

作者信息

Kaplanai Entzy, Tzouras Nikolaos V, Tsoureas Nikolaos, Bracho Pozsoni Nestor, Bhandary Subhrajyoti, Van Hecke Kristof, Nolan Steven P, Vougioukalakis Georgios C

机构信息

Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, 15771, Athens, Greece.

Department of Chemistry and Centre of Sustainable Chemistry, Ghent University, Krijgslaan 281, S-3, 9000 Ghent, Belgium.

出版信息

Dalton Trans. 2024 Jul 2;53(26):11001-11008. doi: 10.1039/d4dt01414f.

DOI:10.1039/d4dt01414f
PMID:38874579
Abstract

Carbene-metal-amide (CMA) complexes of gold, silver, and copper have been studied extensively for their photochemical/photocatalytic properties and as potential (pre-)catalysts in organic synthesis. Herein, the design, synthesis, and characterization of five bench-stable Au-, Ag-, and Cu-NHC complexes bearing the benzotriazolyl anion as an amide donor, are reported. All complexes are synthesized in a facile and straightforward manner, using mild conditions. The catalytic activity of the Ag and Cu complexes was studied in propargylamide cycloisomerization and carbonyl hydrosilylation reactions. Both CMA-catalyzed transformations proceed under mild conditions and are highly efficient for a range of propargylamides and carbonyl compounds, respectively, affording the desired corresponding products in good to excellent yields.

摘要

金、银和铜的卡宾-金属-酰胺(CMA)配合物因其光化学/光催化性质以及作为有机合成中的潜在(预)催化剂而受到广泛研究。在此,报道了五种带有苯并三唑基阴离子作为酰胺供体的稳定性良好的金、银和铜-NHC配合物的设计、合成及表征。所有配合物均采用温和条件,以简便直接的方式合成。研究了银和铜配合物在炔丙酰胺环异构化和羰基氢化硅烷化反应中的催化活性。两种CMA催化的转化反应均在温和条件下进行,分别对一系列炔丙酰胺和羰基化合物具有高效性,以良好至优异的产率得到所需的相应产物。

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