Stereoretentive Palladium‐Catalyzed Arylation,Alkenylation, and Alkynylation of 1‐Thiosugars and Thiols Using Aminobiphenyl Palladacycle Precatalyst at Room Temperature |
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Authors: | Alexandre Bruneau Dr Maxime Roche Dr Abdallah Hamze Dr Jean‐Daniel Brion Dr Mouad Alami Dr Samir Messaoudi |
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Institution: | 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, Chatenay‐Malabry, 92296 (France) |
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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. |
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Keywords: | arylthioglycosides bond‐forming reactions thiols palladacycles unprotected thiosugars |
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