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

Research output: Contribution to journalArticleResearchpeer-review

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.
Original languageEnglish
Pages (from-to)331-336
JournalAdvanced Synthesis & Catalysis
Volume362
DOIs
Publication statusPublished - 2020

Fields of Expertise

  • Human- & Biotechnology

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