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芳香分子合成中多功能且具策略性的——氨基甲酸酯导向金属化基团：最新进展

The Versatile and Strategic -Carbamate Directed Metalation Group in the Synthesis of Aromatic Molecules: An Update.

作者信息

Jansen-van Vuuren Ross D, Liu Susana, Miah M A Jalil, Cerkovnik Janez, Košmrlj Janez, Snieckus Victor

机构信息

Department of Chemistry, Queen's University, Chernoff Hall, 9 Bader Lane, Kingston, Ontario K7K 2N1, Canada.

Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000 Ljubljana, Slovenia.

出版信息

Chem Rev. 2024 Jun 26;124(12):7731-7828. doi: 10.1021/acs.chemrev.3c00923. Epub 2024 Jun 12.

DOI:10.1021/acs.chemrev.3c00923
PMID:38864673
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11212060/
Abstract

The aryl -carbamate (ArOAm) group is among the strongest of the directed metalation groups (DMGs) in directed metalation (DM) chemistry, especially in the form Ar-OCONEt. Since the last comprehensive review of metalation chemistry involving ArOAms (published more than 30 years ago), the field has expanded significantly. For example, it now encompasses new substrates, solvent systems, and metalating agents, while conditions have been developed enabling metalation of ArOAm to be conducted in a green and sustainable manner. The ArOAm group has also proven to be effective in the anionic -Fries (AF) rearrangement, Directed remote metalation (DM), iterative DM sequences, and DM-halogen dance (HalD) synthetic strategies and has been transformed into a diverse range of functionalities and coupled with various groups through a range of cross-coupling (CC) strategies. Of ultimate value, the ArOAm group has demonstrated utility in the synthesis of a diverse range of bioactive and polycyclic aromatic compounds for various applications.

摘要

芳基氨基甲酸酯（ArOAm）基团是导向金属化（DM）化学中最强的导向金属化基团（DMG）之一，尤其是Ar-OCONEt形式。自从上次对涉及ArOAm的金属化化学进行全面综述（30多年前发表）以来，该领域已显著扩展。例如，它现在涵盖了新的底物、溶剂体系和金属化试剂，同时已经开发出一些条件，使ArOAm的金属化能够以绿色和可持续的方式进行。ArOAm基团在阴离子-Fries（AF）重排、导向远程金属化（DM）、迭代DM序列以及DM-卤素迁移（HalD）合成策略中也已证明是有效的，并且已通过一系列交叉偶联（CC）策略转化为多种官能团并与各种基团偶联。最具价值的是，ArOAm基团已在合成各种用于不同应用的生物活性和多环芳族化合物中显示出实用性。

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7
Organogel delivery vehicles for the stabilization of organolithium reagents.用于稳定有机锂试剂的有机凝胶输送载体。
Nat Chem. 2023 Mar;15(3):319-325. doi: 10.1038/s41557-023-01136-x. Epub 2023 Feb 16.
8
Sustainable and practical formation of carbon-carbon and carbon-heteroatom bonds employing organo-alkali metal reagents.利用有机碱金属试剂可持续且实用地形成碳-碳键和碳-杂原子键。
Chem Sci. 2022 Dec 21;14(6):1342-1362. doi: 10.1039/d2sc05475b. eCollection 2023 Feb 8.
9
What is a Cross-Coupling? An Argument for a Universal Definition.什么是交叉偶联？关于通用定义的探讨。
Tetrahedron. 2023 Jan 9;130. doi: 10.1016/j.tet.2022.133176. Epub 2022 Nov 29.
10
Design, synthesis and evaluation of quinoline--carbamate derivatives as multifunctional agents for the treatment of Alzheimer's disease.设计、合成及评估喹啉-氨基甲酸酯衍生物作为治疗阿尔茨海默病的多功能药物。
J Enzyme Inhib Med Chem. 2023 Dec;38(1):2169682. doi: 10.1080/14756366.2023.2169682.