通过直接形成 C(sp3)-N(sp3)键进行区域特异性交叉脱氢偶联，对 BODIPYs 进行介甲基胺化。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-09-06 Epub Date: 2024-06-14 DOI:10.1021/acs.orglett.4c01233

Kartik Dutta, Amey P Wadawale, Soumyaditya Mula

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引用次数: 0

摘要

在此，我们报告了利用 PIDA 作为氧化剂与多种脂肪族仲胺通过 C(sp3)-N(sp3)键的形成对 BODIPY 染料进行直接间甲基胺化的方法。在 C1、C3、C5 和 C7 甲基存在的情况下，这种无金属交叉脱氢偶联反应在 BODIPY 的中甲基位置上具有区域特异性。为了确定反应机理和反应的区域特异性，研究人员进行了详细的核磁共振波谱分析、高分辨率质谱分析和 X 射线晶体学研究。最后，对新合成的染料的光物理和电化学性质进行了评估和合理化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

meso-Methyl Amination of BODIPYs by Regiospecific Cross Dehydrogenative Coupling via Direct C(sp3)-N(sp3) Bond Formation.

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meso-Methyl Amination of BODIPYs by Regiospecific Cross Dehydrogenative Coupling via Direct C(sp³)-N(sp³) Bond Formation.

Herein, we report a direct meso-methyl amination of BODIPY dyes by C(sp³)-N(sp³) bond formation using PIDA as an oxidant with a wide range of aliphatic secondary amines. This metal free cross dehydrogenative coupling reaction is regiospecific at the meso-methyl position of BODIPY in the presence of C1, C3, C5, and C7 methyl groups. Detailed nuclear magnetic resonance spectroscopy, high-resolution mass spectrometry, and X-ray crystallographic studies were performed to establish the reaction mechanism and the regiospecificity of the reaction. Finally, the photophysical and electrochemical properties of the newly synthesized dyes were evaluated and rationalized.

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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.