Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction
Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction
复制标题
草酸二酰胺和叔丁醇：两种类型的配体能够通过铜催化的偶联反应实际获得烷基芳基醚
DOI：
10.1021/jacs.8b12142
复制
发表时间：
2019-02-27
影响因子：
15
通讯作者：
Ma, Dawei
中科院分区：
文献类型：
--
作者：
Chen, Zhixiang;Jiang, Yongwen;Ma, Dawei
建立了一种稳健实用的制备烷基芳基醚的方案，该方案依赖于使用两种类型的配体来促进cu催化（杂）芳基卤化物的烷氧基化。反应范围是非常普遍的各种偶联伙伴，特别是挑战性仲醇和（杂）芳酰氯。在与芳酰氯和溴化物偶联的情况下，两种草酸二胺作为强力配体。叔丁醇首次被证明是铜催化偶联反应的配体，导致芳基碘化物在室温下完全烷氧基化。此外，许多碳水化合物衍生物适用于该偶联反应，其产率为29-98%。
A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcohols and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic diamides serve as the powerful ligands. The tert-butoxide is first demonstrated as a ligand for Cu-catalyzed coupling reaction, leading to alkoxylation of aryl iodides complete at room temperature. Additionally, a number of carbohydrate derivatives are applicable for this coupling reaction, affording the corresponding carbohydrate-aryl ethers in 29-98% yields.