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释放水溶性金（I）-氮杂环卡宾配合物的潜力：揭示羧酸在炔基氨基酸衍生物环异构化中的作用。

Unlocking the potential of water-soluble gold(i)-NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivatives.

作者信息

Pérez Liddier O, Dómina Tomás A, Fernández Gabriela A, Silbestri Gustavo F, Testero Sebastián A

机构信息

Instituto de Química Rosario-IQUIR (CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario Suipacha 531 Rosario S2002LRK Argentina

Departamento de Química, INQUISUR, Universidad Nacional del Sur (UNS)-CONICET B8000CPB Bahía Blanca Argentina

出版信息

RSC Adv. 2024 Aug 6;14(34):24643-24651. doi: 10.1039/d4ra04876h. eCollection 2024 Aug 5.

DOI:10.1039/d4ra04876h
PMID:39108960
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11302150/
Abstract

Hydrocarboxylation of alkyne-containing amino acid derivatives using water-soluble gold(i)-NHC complexes in an aqueous biphasic system at room temperature is described. Addition of silver salts is not required as the carboxylic acid group of the substrate is responsible for the activation of the gold catalyst at room temperature. Our results confirm that the steric bulk of the -heterocyclic carbene ligands is an important factor in both the stability and the catalytic activity of gold(i) complexes in aqueous medium, and consequently in the recycling (at least 15 times without any loss of activity). The catalytic activity of our most active water-soluble gold(i)-NHC complex has been demonstrated in the cycloisomerization of amino acids derivatives with terminal and internal alkynes in aqueous media at room temperature.

摘要

描述了在室温下于双水相体系中使用水溶性金（I）-N-杂环卡宾配合物对含炔基氨基酸衍生物进行氢羧化反应。由于底物的羧酸基团在室温下负责金催化剂的活化，因此无需添加银盐。我们的结果证实，-杂环卡宾配体的空间位阻是金（I）配合物在水性介质中的稳定性和催化活性的重要因素，因此也是其循环利用（至少15次且活性无任何损失）的重要因素。我们最具活性的水溶性金（I）-N-杂环卡宾配合物的催化活性已在室温下于水性介质中对具有末端炔烃和内炔烃的氨基酸衍生物的环异构化反应中得到证明。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63bd/11302150/31cfb91be1bb/d4ra04876h-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63bd/11302150/04a2e60c2d95/d4ra04876h-f1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63bd/11302150/4d3018dbc917/d4ra04876h-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63bd/11302150/19594d4a73b9/d4ra04876h-s2.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63bd/11302150/a7e00499a5da/d4ra04876h-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63bd/11302150/31cfb91be1bb/d4ra04876h-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63bd/11302150/04a2e60c2d95/d4ra04876h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63bd/11302150/70f682be71ea/d4ra04876h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63bd/11302150/2001f9cfa096/d4ra04876h-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63bd/11302150/fd693668f089/d4ra04876h-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63bd/11302150/4d3018dbc917/d4ra04876h-f4.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63bd/11302150/31cfb91be1bb/d4ra04876h-f6.jpg

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本文引用的文献

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Optimizing Catalyst and Reaction Conditions in Gold(I) Catalysis-Ligand Development.优化金（I）催化中的催化剂和反应条件-配体开发。
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Cycloisomerization of π-Coupled Heteroatom Nucleophiles by Gold Catalysis: En Route to Regiochemically Defined Heterocycles.金催化的π 键偶联杂原子亲核试剂的环异构化：通向区域化学定义的杂环。
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优化金（I）催化中的催化剂和条件——抗衡离子和添加剂效应。
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Enantioselective Construction of Functionalized Tetrahydrocarbazoles Enabled by Asymmetric Relay Catalysis of Gold Complex and Chiral Brønsted Acid.手性金配合物和手性布朗斯特酸不对称接力催化构建功能化四氢咔唑
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