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Fluoride-Mediated Aryne 1,2-Difunctionalization Involving C═S Bond Heterolysis.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2024 Jul 19; Vol. 89 (14), pp. 10047-10053. Date of Electronic Publication: 2024 Jul 01. - Publication Year :
- 2024
-
Abstract
- We have successfully synthesized a series of bidentate ligands by utilizing 2-(trimethylsilyl)phenyl trifluorosulfonate as a precursor for the benzyl group. This method proceeded by inserting a polythiourea into the C═S π-bond, intramolecular ring proton migration, and ring opening. Salient features of this strategy are mild reaction conditions, a novel product structure, excellent stereochemistry, and a good functional group tolerance. Furthermore, a series of density functional theory calculations were performed to gain insights into the transfer mechanism.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 89
- Issue :
- 14
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 38951997
- Full Text :
- https://doi.org/10.1021/acs.joc.4c00894