Copper-Catalyzed Transfer Hydrodeuteration of Aryl Alkenes with Quantitative Isotopomer Purity Analysis by Molecular Rotational Resonance Spectroscopy
Originally Published in Analytical Chemistry, May 2021
Authors: Zoua Pa Vang; Albert Reyes; Reilly Sonstrom; Martin S. Holdren; Samantha E. Sloane; Isabella Y Alansari, Justin L. Neill; Brooks H. Pate; Joseph R. Clark
Publication Summary
Originally published in the Journal of the American Chemical Society, this publication describes a copper-catalyzed transfer hydrodeuteration reaction that selectively incorporates one hydrogen atom and one deuterium atom across aryl alkenes. The methodology was demonstrated across a variety of internal and terminal alkene substrates and provides a highly selective route to precisely deuterated molecules, an important class of compounds for pharmaceutical, analytical, and mechanistic research applications.
The study also showcases the use of molecular rotational resonance (MRR) spectroscopy for quantitative isotopomer purity analysis. By combining broadband and cavity-enhanced MRR measurements, the researchers established a high-throughput analytical workflow capable of detecting isotopic impurities with exceptional precision while significantly reducing sample consumption and analysis time. The results demonstrate outstanding regioselectivity and highlight the value of MRR spectroscopy for verifying isotopic composition in deuteration chemistry.
Key Takeaways
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A copper-catalyzed transfer hydrodeuteration method enables highly selective incorporation of hydrogen and deuterium across aryl alkenes.
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The reaction was successfully applied to a range of alkene substrates, demonstrating broad utility and versatility.
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MRR spectroscopy provides precise quantitative analysis of isotopomer purity, helping identify and measure isotopic impurities that may be difficult to evaluate using conventional techniques.
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A cavity-enhanced MRR workflow reduces sample requirements and analysis time, making high-throughput isotopic characterization more practical.
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The analytical approach delivers highly accurate measurements of reaction selectivity, supporting confidence in precision deuteration workflows.
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The work highlights the complementary role of MRR spectroscopy in synthetic chemistry, providing detailed isotopic characterization alongside traditional analytical methods.