α-Amination at BODIPY and BOPHY Core via Metal-Free Regiospecific Cross Dehydrogenative Coupling Reaction Toward the Development of Lysotracker.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-01 DOI:10.1021/acs.orglett.5c02190

Kartik Dutta,Richa Agrawal,Nitish Chauhan,Bhaskar Das,Amey P Wadawale,Mahesh Subramanian,Soumyaditya Mula

引用次数: 0

Abstract

We report a metal-free, efficient, and quick cross dehydrogenative coupling (CDC) methodology using phenyliodine(III) diacetate (PIDA) as an oxidant to synthesize regiospecific α-amino BODIPYs/BOPHYs via C(sp2)-N(sp3) bond formation. Twenty-seven coupled products were synthesized using different primary/secondary amines and commercial drug molecules. The regiospecificity and mechanism of the reactions were confirmed by NMR, EPR, HRMS, and X-ray crystallography studies. One of the synthesized molecules, BODIPY 3t, showed an excellent lysosome targeting ability with turn-on fluorescence inside the lysosome, making it an efficient Lysotracker agent.

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无金属区域特异性交叉脱氢偶联反应在BODIPY和BOPHY核心上的α-胺化研究

我们报道了一种无金属、高效、快速的交叉脱氢偶联（CDC）方法，使用苯基碘（III）二乙酸酯（PIDA）作为氧化剂，通过C(sp2)-N（sp3）键形成合成区域特异性α-氨基BODIPYs/BOPHYs。利用不同的伯/仲胺和商业药物分子合成了27个偶联产物。通过NMR、EPR、HRMS和x射线晶体学研究证实了反应的区域特异性和机理。其中合成的分子BODIPY 3t表现出优异的溶酶体靶向能力，在溶酶体内部开启荧光，使其成为一种高效的溶酶追踪剂。

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.