The Versatile and Strategic O-Carbamate Directed Metalation Group in the Synthesis of Aromatic Molecules: An Update,Chemical Reviews

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The Versatile and Strategic O-Carbamate Directed Metalation Group in the Synthesis of Aromatic Molecules: An Update
Chemical Reviews ( IF 51.4 ) Pub Date : 2024-06-12 , DOI: 10.1021/acs.chemrev.3c00923
Ross D Jansen-van Vuuren _{1,

2} , Susana Liu ₁ , M A Jalil Miah ₃ , Janez Cerkovnik ₂ , Janez Košmrlj ₂ , Victor Snieckus ₁

Affiliation

The aryl O-carbamate (ArOAm) group is among the strongest of the directed metalation groups (DMGs) in directed ortho metalation (DoM) chemistry, especially in the form Ar-OCONEt₂. 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 ortho-Fries (AoF) rearrangement, Directed remote metalation (DreM), iterative DoM sequences, and DoM-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.

中文翻译：

芳香族分子合成中多功能且战略性的邻氨基甲酸酯定向金属化基团：最新进展

芳基O-氨基甲酸酯(ArOAm)基团是定向邻位金属化(D o M)化学中最强的定向金属化基团(DMG)之一，尤其是Ar-OCONEt ₂形式。自从上一次涉及 ArOAms 的金属化化学综合综述（30 多年前发表）以来，该领域已显着扩展。例如，它现在涵盖新的基材、溶剂系统和金属化剂，同时已经开发出使 ArOAm 金属化能够以绿色和可持续的方式进行的条件。 ArOAm 基团还被证明在阴离子邻位-Fries (A o F) 重排、定向远程金属化 (D re M)、迭代Do M 序列和Do M-卤素舞 (HalD) 合成策略中有效。已转变为多种功能，并通过一系列交叉耦合（CC）策略与各种组耦合。 ArOAm 基团具有最终价值，已在合成各种生物活性和多环芳香族化合物的各种应用中展现出实用性。

更新日期：2024-06-12

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