Sciencemadness Discussion Board

arylation of 2-methyl pryridine

rotwang - 9-7-2006 at 17:49

2-methyl pyridine (alpha picoline) loses a proton from the 2 methyl group and forms a stabilised anion when treated with sodamide or other strong base.
this anion can then react with an alkyl halide to give an 2-alkyl pyridine with an extended carbon chain.

has anyone come across a reaction in their travels where an aryl diazonium salt or a aryl halide or sulphonic acid is reacted with the anion generated from 2-methyl pyridine? In theory this would generate a 2-benzyl pyridine. would appreciate any help

BTW I know that benzyl pyridines are easy to synthesise from pyridine and benzyl lithium, its just a little more complex than that.

-R