Hypervalent Iodine-Mediated Selective Monofunctionalization of Calix[4]arenes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-30 DOI:10.1021/acs.orglett.5c01121

Haoliang Hao, Wei Zhang, Wenjie Zhu, Wenjing Bao, Guangxing Gu, Yanchuan Zhao

引用次数: 0

Abstract

The selective introduction of a single functionality on the upper rim of calix[4]arene is challenging due to the identical reactivity of its four aryl units. In this study, we introduce a novel strategy for monofunctional modification of calix[4]arenes using a hypervalent iodine-mediated C–H functionalization. This process yields a calix[4]arene-iodonium salt, which can be easily isolated due to its distinct solubility compared to the native calixarene. This versatile intermediate efficiently undergoes C–O, C–N, and C–S couplings with a variety of nucleophiles, including amines, phenols, thiols, and sulfinate salts under mild conditions. This strategy enables streamlined structural diversification of calix[4]arenes, opening new avenues for the design of supramolecular macrocycles with tailored functions.

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高价碘介导杯萼芳烃选择性单功能化

由于其四个芳基单元具有相同的反应活性，因此在杯状[4]芳烃的上缘选择性引入单一功能是具有挑战性的。在这项研究中，我们介绍了一种利用高价碘介导的C-H功能化对杯状[4]芳烃进行单功能修饰的新策略。该过程产生杯芳烃碘盐，由于其与天然杯芳烃相比具有明显的溶解度，因此可以很容易地分离。这种多功能中间体在温和的条件下能有效地与多种亲核试剂（包括胺、酚、硫醇和亚硫酸盐）偶联C-O、C-N和C-S。这一策略使杯状[4]芳烃的流线型结构多样化，为设计具有定制功能的超分子大环开辟了新的途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

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.