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

Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

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.
Originalspracheenglisch
FachzeitschriftAdvanced Synthesis & Catalysis
DOIs
PublikationsstatusVeröffentlicht - 2019

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Nucleophiles
Antibiotics
Sulfhydryl Compounds
Functional groups
Catalysts
Substrates
Sulfides
Cephalosporins
Anti-Bacterial Agents

Fields of Expertise

  • Human- & Biotechnology

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title = "Pd/BIPHEPHOS is an Efficient Catalyst for the Pd‐Catalyzed S‐Allylation of Thiols with High n‐Selectivity",
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.",
author = "Thomas Schlatzer and Hilmar Schr{\"o}der and Melanie Trobe and Christian Lembacher-Fadum and Simon Stangl and Christoph Schl{\"o}gl and Hansj{\"o}rg Weber and Rolf Breinbauer",
year = "2019",
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T1 - Pd/BIPHEPHOS is an Efficient Catalyst for the Pd‐Catalyzed S‐Allylation of Thiols with High n‐Selectivity

AU - Schlatzer, Thomas

AU - Schröder, Hilmar

AU - Trobe, Melanie

AU - Lembacher-Fadum, Christian

AU - Stangl, Simon

AU - Schlögl, Christoph

AU - Weber, Hansjörg

AU - Breinbauer, Rolf

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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.

U2 - https://doi.org/10.1002/adsc.201901250

DO - https://doi.org/10.1002/adsc.201901250

M3 - Article

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

SN - 1615-4150

ER -