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Bruneau A, Roche M, Hamze A, et al. Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature. Chemistry. 2015;21(23):8375-9doi: 10.1002/chem.201501050.
Bruneau, A., Roche, M., Hamze, A., Brion, J. D., Alami, M., & Messaoudi, S. (2015). Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature. Chemistry (Weinheim an der Bergstrasse, Germany), 21(23), 8375-9. https://doi.org/10.1002/chem.201501050
Bruneau, Alexandre, et al. "Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,23 (2015): 8375-9. doi: https://doi.org/10.1002/chem.201501050
Bruneau A, Roche M, Hamze A, Brion JD, Alami M, Messaoudi S. Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature. Chemistry. 2015 Jun 01;21(23):8375-9. doi: 10.1002/chem.201501050. Epub 2015 Apr 15. PMID: 25876554.
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Chemistry. 2015 Jun 01;21(23):8375-9. doi: 10.1002/chem.201501050. Epub 2015 Apr 15.

Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature.

Chemistry (Weinheim an der Bergstrasse, Germany)

Alexandre Bruneau, Maxime Roche, Abdallah Hamze, Jean-Daniel Brion, Mouad Alami, Samir Messaoudi

Affiliations

  1. Univ. Paris-Sud, CNRS, BioCIS-UMR 8076, Laboratoire de Chimie Thérapeutique, Equipe Labellisée Ligue Contre le Cancer, LabEx LERMIT Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, 92296 (France).
  2. Univ. Paris-Sud, CNRS, BioCIS-UMR 8076, Laboratoire de Chimie Thérapeutique, Equipe Labellisée Ligue Contre le Cancer, LabEx LERMIT Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, 92296 (France). [email protected].
  3. Univ. Paris-Sud, CNRS, BioCIS-UMR 8076, Laboratoire de Chimie Thérapeutique, Equipe Labellisée Ligue Contre le Cancer, LabEx LERMIT Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, 92296 (France). [email protected].

PMID: 25876554 DOI: 10.1002/chem.201501050

Abstract

A general and efficient protocol for the palladium-catalyzed functionalization of mono- and polyglycosyl thiols by using the palladacycle precatalyst G3-XantPhos was developed. The C-S bond-forming reaction was achieved rapidly at room temperature with various functionalized (hetero)aryl-, alkenyl-, and alkynyl halides. The functional group tolerance on the electrophilic partner is typically high and anomer selectivities of thioglycosides are high in all cases studied. New sulfur nucleophiles such as thiophenols, alkythiols, and thioaminoacids (cysteine) were also successfully coupled to lead to the most general and practical method yet reported for the functionalization of thiols.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: arylthioglycosides; bond-forming reactions; palladacycles; thiols; unprotected thiosugars

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