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).
Chemistry. 2015 Jun 1;21(23):8375-9. doi: 10.1002/chem.201501050. Epub 2015 Apr 15.
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.
开发了一种通用且高效的方法，使用钯配合物前催化剂 G3-XantPhos，通过单糖和多糖基硫醇的钯催化官能化。在室温下，通过各种功能化（杂）芳基、烯基和炔基卤化物，快速实现 C-S 键形成反应。亲电试剂的官能团耐受性通常较高，在所研究的所有情况下，硫糖苷的非对映选择性都很高。新的硫亲核试剂，如硫酚、硫醇和硫代氨基酸（半胱氨酸），也成功地与硫醇进行偶联，得到了迄今为止报道的最通用和实用的硫醇官能化方法。
