Ethyl Pinacol Boronates as Advantageous Precursors for Copper-Mediated Radiofluorination

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-10 DOI:10.1021/acs.orglett.5c0205510.1021/acs.orglett.5c02055

Nikolaos Hadjipaschalis, Sebastiano Ortalli, Zijun Chen, Robert S. Paton, Joseph Ford*, Matthew Tredwell* and Véronique Gouverneur*,

引用次数: 0

Abstract

(Hetero)aryl pinacol boronic esters are routinely used for ¹⁸F-labeling and have accelerated numerous diagnostic and drug discovery programs. An analysis of the current state-of-play, however, highlights a pending challenge. Reports have indicated that some pinacol boronic esters are unstable and difficult to purify, hindering broader adoption in the clinic. Herein, we demonstrate that more stable boronic esters derived from 3,4-diethylhexane-3,4-diol (Epin) are highly suitable for copper-mediated radiolabeling. Impact is illustrated with the automated synthesis of [¹⁸F]FMZ.

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乙酯硼酸酯作为铜介导的放射性氟化的有利前体

（杂）芳基萘酚硼酯通常用于18f标记，并加速了许多诊断和药物发现项目。然而，对当前形势的分析凸显了一个悬而未决的挑战。有报道指出，一些匹纳科尔硼酯不稳定且难以纯化，阻碍了其在临床上的广泛应用。在此，我们证明了由3,4-二乙基己烷-3,4-二醇（Epin）衍生的更稳定的硼酯非常适合于铜介导的放射性标记。影响用[18F]FMZ的自动合成来说明。

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.