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*

*Corresponding author for this work

Research output: Contribution to journalArticle

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.).

Original languageEnglish
Pages (from-to)331-336
Number of pages6
JournalAdvanced Synthesis & Catalysis
Volume362
Issue number2
DOIs
Publication statusPublished - 23 Jan 2020

Keywords

  • crossover
  • isofunctional reaction
  • isomerization
  • thioether
  • Tsuji-Trost allylation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fields of Expertise

  • Human- & Biotechnology

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