Mechanistic insights into the base-mediated deuteration of pyridyl phosphonium and ammonium salts
Pyridines can be deuterated at the remote sites by treatment with KO<i>t</i>Bu in DMSO-<i>d</i> <sub>6</sub>, although without discrimination between the <i>meta</i>- and <i>para</i>-position. Herein, base-catalyzed deuterations have been studied, computationally and experimentally, using a series of pyridyl phosphonium salts with a temporary electron-withdrawing group to block the <i>para</i>-position while increasing the acidity in the other positions.
Authors
- Valerio Fasano (ORCID: https://orcid.org/0000-0003-1819-4483)
- Andrea Citarella (ORCID: https://orcid.org/0000-0001-5881-7142)
- Daniele Passarella (ORCID: https://orcid.org/0000-0001-6180-9581)
- Delia Blasi (ORCID: https://orcid.org/0000-0003-1561-6572)
- Paolo Ronchi
- Alessandro Dimasi (ORCID: https://orcid.org/0009-0008-0211-9327)
- Sergio Rossi (ORCID: https://orcid.org/0000-0002-2694-9535)
- Arianna Montoli (ORCID: https://orcid.org/0009-0008-1317-2158)
- Miriana guarnaccia
Institutions
- University of Milan (IT)
- Chiesi (Italy) (IT)
Publication Details
- Journal
- RSC Advances
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d4ra07557a
- Citations
- 2
- Primary Topic
- Chemical Reactions and Isotopes
- Type
- article
- Field-Weighted Citation Impact
- 1.58
Funders
- Chiesi Farmaceutici
- Università degli Studi di Milano
- University of Leicester