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 …

CL Fraser, NR Anastasi, JJS Lamba

Index: Fraser, Cassandra L.; Anastasi, Natia R.; Lamba, Jaydeep J. S. Journal of Organic Chemistry, 1997 , vol. 62, # 26 p. 9314 - 9317

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Citation Number: 63

Abstract

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 TMSCl to generate 4, 4'-bis [(trimethylsilyl) methyl]-2, 2'-bpy (1). The TMS ...