Hydro/Fluoro-phosphoro(di)thiolation of Allenamides: Toward S <sub>N</sub> 2-Selective Transition-Metal-Free Formal Hydrocarbonation
Two versatile synthetic strategies for β-H/F-enamide-tagged phosphoro(di)thioates from allenamides are disclosed, relying on electrophilic activation via β-H and F-iminium species. These developed straightforward protocols demonstrate broad applicability in complex molecular contexts with remarkable chemo- and regioselectivity. The synthesized allylphosphorothioates (APTs) act as potent electrophiles, enabling S<sub>N</sub>2-selective allylic substitution with (hard)C-nucleophiles of all hybridizations to deliver hydrocarbonation products in seamless complement to transition-metal-driven strategies.
Authors
- Jin Kyoon Park (ORCID: https://orcid.org/0000-0001-6768-2788)
- Tapas R. Pradhan (ORCID: https://orcid.org/0000-0003-1480-7799)
- Raju Teegala
- Kadiyala Sagar
- Arun B. Ingle
- Purna C. R. Bhavnari
Institutions
- Seoul National University (KR)
- Institute of Medicinal Plant Development (CN)
- GITAM University (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-01-26
- DOI
- https://doi.org/10.1021/acs.orglett.5c05174
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.00