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
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.
Marsais, Francis,Breant, Patrice,Ginguene, Alain,Queguiner, Guy
p. 139 - 147
(2007/10/02)
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