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Deuterodehalogenation Under Net Reductive or Redox‐Neutral Conditions Enabled by Paired ElectrolysisWood, Devin; Lin, Song
Angewandte Chemie (International ed.), April 3, 2023, Letnik: 62, Številka: 15Journal Article
Interest in deuterated active pharmaceutical ingredients (APIs) is increasing as deuteration holds promise for kinetic isotope effect (KIE) regulated fine‐tuning of API performance. Moreover, deuterium isotope labeling is frequently carried out to study organic and bioorganic reaction mechanisms and to facilitate complex target synthesis. As such, methods for highly selective deuteration of organic molecules are highly desirable. Herein, we present an electrochemical method for the selective deuterodehalogenation of benzylic halides via a radical‐polar crossover mechanism, using inexpensive deuterium oxide (D2O) as the deuterium source. We demonstrate broad functional group compatibility across a range of aryl and heteroaryl benzylic halides. Furthermore, we uncover a sequential paired electrolysis regime, which permits switching between net reductive and overall redox‐neutral reactions of sulfur‐containing substrates simply by changing the identity of the sacrificial reductant employed. Site‐specific introduction of deuterium is important in organic and medicinal chemistry. Herein, we present an electrochemical method for the deuterodehalogenation of aryl and heteroaryl benzylic halides, using inexpensive deuterium oxide as the deuterium source. We also uncover a sequential paired electrolysis regime, which permits switching between net reductive and overall redox‐neutral reactions of sulfur‐containing substrates.
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JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
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