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- Title
Metallaphotoredox deuteroalkylation utilizing thianthrenium salts.
- Authors
Jiao, Mengjie; Zhang, Jie; Wang, Minyan; Lu, Hongjian; Shi, Zhuangzhi
- Abstract
Deuterium labeling compounds play a crucial role in organic and pharmaceutical chemistry. The synthesis of such compounds typically involves deuterated building blocks, allowing for the incorporation of deuterium atoms and functional groups into a target molecule in a single step. Unfortunately, the limited availability of synthetic approaches to deuterated synthons has impeded progress in this field. Here, we present an approach utilizing alkyl-substituted thianthrenium salts that efficiently and selectively introduce deuterium at the α position of alkyl chains through a pH-dependent HIE process, using D2O as the deuterium source. The resulting α-deuterated alkyl thianthrenium salts, which bear two deuterium atoms, exhibit excellent selectivity and deuterium incorporation in electrophilic substitution reactions. Through in situ formation of isotopically labelled alkyl halides, these thianthrenium salts demonstrate excellent compatibility in a series of metallaphotoredox cross-electrophile coupling with (hetero)aryl, alkenyl, alkyl bromides, and other alkyl thianthrenium salts. Our technique allows for a wide range of substrates, high deuterium incorporation, and precise control over the site of deuterium insertion within a molecule such as the benzyl position, allylic position, or any alkyl chain in between, as well as neighboring heteroatoms. This makes it invaluable for synthesizing various deuterium-labeled compounds, especially those with pharmaceutical significance. Deuterium labeling compounds play a crucial role in organic and pharmaceutical chemistry but the limited availability of synthetic approaches to deuterated synthons has impeded progress in this field. Here, the authors present an approach utilizing alkyl-substituted aryl thianthrenium salts that efficiently and selectively introduce deuterium at the α position of alkyl chains through a pH-dependent hydrogen isotope exchange process, using D2O as the deuterium source.
- Subjects
ELECTROPHILIC substitution reactions; HYDROGEN isotopes; DEUTERIUM compounds; ELECTROPHILES; PHARMACEUTICAL chemistry; HALOALKANES
- Publication
Nature Communications, 2024, Vol 15, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-024-48590-w