Mild and Chemoselective Triethylsilane-Mediated Debenzylation for Phosphate Synthesis
The synthetic utility of tetrabenzyl pyrophosphate for achieving chemoselective phosphorylation of phenols, as well as primary, secondary, and tertiary alcohols, is reported here. Additionally, we introduce a rapid, mild, and chemoselective debenzylation procedure, enabling access to phosphates in the presence of redox sensitive groups. Finally, stoichiometrically controlled monodebenzylation provides a versatile platform for late-stage divergent synthesis of phosphodiester and phosphoramidate chemical libraries.
Authors
- Luke Hodson (ORCID: https://orcid.org/0000-0001-9779-1133)
- Nicole Pribut (ORCID: https://orcid.org/0000-0003-0439-9162)
- Dennis C. Liotta
- David Laws (ORCID: https://orcid.org/0000-0001-5828-717X)
- Leon Jacobs (ORCID: https://orcid.org/0000-0002-8717-3654)
- Gouthami Pashikanti (ORCID: https://orcid.org/0009-0002-9015-2413)
- Aletta E. van der Westhuyzen
- Paul Joseph Tholath
Institutions
- Emory University (US)
- Université Bourgogne Franche-Comté (FR)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-24
- DOI
- https://doi.org/10.1021/acs.orglett.4c04258
- Primary Topic
- Organophosphorus compounds synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Emory University
- Georgia Research Alliance