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Abstract
The Pd-catalyzed S-allylation of thiols with stable allylcarbonate and allylacetate reagents offers several advantages over established reactions for the formation of thioethers. We could demonstrate that Pd/BIPHEPHOS is a catalyst system which allows the transition metal-catalyzed S-allylation of thiols with excellent n-regioselectivity. Mechanistic studies showed that this reaction is reversible under the applied reaction conditions. The excellent functional group tolerance of this transformation was demonstrated with a broad variety of thiol nucleophiles (18 examples) and allyl substrates (9 examples), and could even be applied for the late-stage diversification of cephalosporins, which might find application in the synthesis of new antibiotics. (Figure presented.).
Originalsprache | englisch |
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Seiten (von - bis) | 331-336 |
Seitenumfang | 6 |
Fachzeitschrift | Advanced Synthesis & Catalysis |
Jahrgang | 362 |
Ausgabenummer | 2 |
DOIs | |
Publikationsstatus | Veröffentlicht - 23 Jan. 2020 |
ASJC Scopus subject areas
- Katalyse
- Organische Chemie
Fields of Expertise
- Human- & Biotechnology
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- 1 Abgeschlossen
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FWF - Peptide - Übergangsmetall-katalysierte post-translationale Modifikation von Peptiden und Proteinen
1/09/16 → 31/07/21
Projekt: Foschungsprojekt