Deuteration of Arenes via Pd-Catalyzed C–H Activation: A Lesson in Nondirected C–H Activation, Isotopic Labeling, and NMR Characterization

IF 2.9 3区教育学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Journal of Chemical Education Pub Date : 2024-07-15 DOI:10.1021/acs.jchemed.4c0027010.1021/acs.jchemed.4c00270

Fritz Deufel, and , Manuel van Gemmeren*,

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Abstract

Isotopic labeling is an important tool in medicinal research, metabolomics, and for understanding reaction mechanisms. In this context, transition metal-catalyzed C–H activation has emerged as a key technology for deuterium incorporation via hydrogen isotope exchange. A detailed and easy-to-implement experimental procedure for a nondirected arene deuteration has been developed that exclusively uses commercial equipment and chemicals. The protocol is ideally suited for students and other prospective applicants who are not experts in catalysis. The degree of deuterium incorporation was analyzed via different means like mass spectrometry and ¹H and ²H nuclear magnetic resonance (NMR). A hands-on understanding of quantitative NMR, as well as the influence of H/D exchange on experimental spectra, was conveyed by comparative NMR spin simulations. Students were measurably familiarized with the concepts of C–H activation, isotope effects, and basics in experimental catalysis.

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通过 Pd 催化 C-H 活化实现烯的氘化：非定向 C-H 活化、同位素标记和 NMR 表征课程

同位素标记是药物研究、代谢组学和了解反应机理的重要工具。在此背景下，过渡金属催化的 C-H 活化技术已成为通过氢同位素交换掺入氘的关键技术。我们开发了一套详细而易于实施的非定向炔氘化实验程序，该程序只使用商业设备和化学品。该方案非常适合非催化专家的学生和其他潜在申请人。通过质谱法、1H 和 2H 核磁共振（NMR）等不同方法分析了氘的掺入程度。通过比较核磁共振自旋模拟，让学生亲身了解定量核磁共振以及 H/D 交换对实验光谱的影响。学生们明显熟悉了 C-H 活化、同位素效应和实验催化基础知识等概念。

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来源期刊

Journal of Chemical Education 化学-化学综合

CiteScore

5.60

自引率

50.00%

发文量

465

审稿时长

6.5 months

期刊介绍： The Journal of Chemical Education is the official journal of the Division of Chemical Education of the American Chemical Society, co-published with the American Chemical Society Publications Division. Launched in 1924, the Journal of Chemical Education is the world’s premier chemical education journal. The Journal publishes peer-reviewed articles and related information as a resource to those in the field of chemical education and to those institutions that serve them. JCE typically addresses chemical content, activities, laboratory experiments, instructional methods, and pedagogies. The Journal serves as a means of communication among people across the world who are interested in the teaching and learning of chemistry. This includes instructors of chemistry from middle school through graduate school, professional staff who support these teaching activities, as well as some scientists in commerce, industry, and government.