77332-78-6Relevant articles and documents
ETUDE DES ortho-METALLATIONS REGIOSELECTIVES DE LA CHLORO-3 PYRIDINE PAR DES ORGANOLITHIENS ET DES AMIDURES DE LITHIUM; EFFET D'ORIENTATION PAR LE SOLVANT, APPLICATIONS A LA SYNTHESE
Marsais, Francis,Breant, Patrice,Ginguene, Alain,Queguiner, Guy
, p. 139 - 147 (1981)
Lithium dialkylamides metalate 3-chloropyridine with excellent regioselectivity at position 4.This reaction occurs in THF solution at -60 deg C and it leads to various 3,4-disubstituted pyridines in good yields.This regioselectivity is completely changed in ether solution by using the butyllithium-TMEDA complex.In that case position 2 is metallated and 2,3-disubstituted pyridines are obtained.