Synthesis of halomethyl and other bipyridine derivatives by reaction of 4,4'-bis[(trimethylsilyl)methyl]-2',2-bipyridine with electrophiles in the presence of fluoride ion

摘要

Bipyridine (bpy) ligands figure prominently in many areas of chemistry. Common precursors to many derivatives are the halomethyl-substituted analogues. This report describes a new, high yield route to these valuable compounds via a trimethylsilyl (TMS) intermediate. 4,4'-Dimethyl- 2,2'-bpy was reacted with lithium diisopropylamide, and the dianion thus formed was trapped with TMSCI to generate 4,4'-bis[(trimethylsilyl)methyl]-2,2'-byp (1).