Alkali-Cation-Selective Arylation Promoted by Ion Recognition of Foldamers

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC
Chenhao Yao, Zhaocheng Xu, Jun Tian, Ze Lin, Changqing Zhang, Yunpeng Ge, Lei Zhang, Siyuan Wang, Zeyuan Dong
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引用次数: 0

Abstract

To explore alkali-cation selectivity at the chemical reaction level, in this work, we for the first time focused on the different behaviors of potassium and sodium ions in intra- and intermolecular arylation. We prepared a series of aromatic foldamers based on pyridine/oxadiazole alternating sequences as the catalysts for the arylation. Our studies revealed that foldamers can selectively recognize K+ over Na+ and the interactions between foldamers and K+ drive the arylation with a significant yield. In contrast, no trace of the product can be found with Na+. Furthermore, foldamers, with biased handedness, can afford products with optical activity. The balance between two enantiomers of products can be freely controlled by the different conformations of foldamers.

Abstract Image

离子识别促进的碱-阳离子选择性芳基化
为了在化学反应水平上探索碱化选择性,本研究首次关注了钾离子和钠离子在分子内和分子间芳基化中的不同行为。我们制备了一系列以吡啶/恶二唑交替序列为基础的芳香折叠物作为芳基化催化剂。我们的研究表明,折叠蛋白可以选择性地识别K+而不是Na+,并且折叠蛋白和K+之间的相互作用驱动了芳基化,并具有显著的产率。相比之下,在Na+中找不到该产物的痕迹。此外,具有偏手性的文件夹可以提供具有光学活性的产品。产物的两种对映体之间的平衡可以由折叠体的不同构象自由控制。
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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