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Multideuteration of Nitroaromatics by Silver-Catalyzed Hydrogen-Isotope Exchange.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2023 Feb 03; Vol. 88 (3), pp. 1560-1567. Date of Electronic Publication: 2023 Jan 12. - Publication Year :
- 2023
-
Abstract
- Silver-catalyzed deuteration of nitroaromatics has been achieved using D <subscript>2</subscript> O as the deuterium source. Distinct from the well-established directing group-guided hydrogen-isotope exchange, this protocol showed an interesting deuteration pattern, where considerable deuterium accumulation was observed around the aromatic rings. Controlling experiments suggested that the deuteration was initiated by a silver-promoted C-H activation. Therefore, a tentative two-stage deuteration mechanism involving aryl-silver species was proposed to explain the deuteration on meta - and para -positions.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 88
- Issue :
- 3
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 36634252
- Full Text :
- https://doi.org/10.1021/acs.joc.2c02618