Synthesis of perfluoroalkylated bipyridines — New ligands for oxidation reactions under fluorous triphasic conditions

✍ Scribed by Silvio Quici; Marco Cavazzini; Silvia Ceragioli; Fernando Montanari; Gianluca Pozzi

• Book ID: 104261308
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 260 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00524-9

✦ Synopsis

Huorous soluble bipyridines bearing two perfluoroalkyiated side chains in the 6,6'-or 4,4'-positions have been prepared in good yields via ethetification of 6,6'-bis(chloromethyl)-2,2'-bipyridine or C-alkylation of 6,6'-dimethyl-2,2'-bipyridine. The new iigands L exhibit amphiphilic behaviour with respect to certain fluorous-organic biphnsic systems. Nevertheless, their ruthenium complexes (RuLn)X generated in situ are efficient catalysts for the epoxidation of trans-stiibene in a fluorous triphnsic system CH2CI2/H20/C8FI8 in the presence of NalO4. The fluorous phase, where (RuLn)X is trapped, can be used up to four times without major loss of catalytic activity.