Pd/BIPHEPHOS is an Efficient Catalyst for the Pd‐Catalyzed S‐Allylation of Thiols with High n‐Selectivity

Thomas Schlatzer, Hilmar Schröder, Melanie Trobe, Christian Lembacher-Fadum, Simon Stangl, Christoph Schlögl, Hansjörg Weber, Rolf Breinbauer*

*Korrespondierende/r Autor/-in für diese Arbeit

Publikation: Beitrag in einer FachzeitschriftArtikelBegutachtung

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.).

Originalspracheenglisch
Seiten (von - bis)331-336
Seitenumfang6
FachzeitschriftAdvanced Synthesis & Catalysis
Jahrgang362
Ausgabenummer2
DOIs
PublikationsstatusVeröffentlicht - 23 Jan. 2020

ASJC Scopus subject areas

  • Katalyse
  • Organische Chemie

Fields of Expertise

  • Human- & Biotechnology

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