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The Structural Proliferation of 2,6‐Difluoropyridine through Organometallic Intermediates
Author(s) -
Schlosser Manfred,
Rausis Thierry
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300649
Subject(s) - chemistry , lithium diisopropylamide , regioselectivity , nucleophile , deprotonation , group 2 organometallic chemistry , halogen , trifluoromethylation , dimethylformamide , halide , organometallic chemistry , aldehyde , organic chemistry , medicinal chemistry , molecule , solvent , catalysis , ion , trifluoromethyl , alkyl
Contrary to a literature claim, 2,6‐difluoropyridine‐3‐carboxaldehyde can be readily prepared by consecutive treatment of 2,6‐difluoropyridine with lithium diisopropylamide and N , N ‐dimethylformamide. Regioselective displacements of fluorine from the aldehyde by nucleophiles were carried out. To demonstrate the versatility of the organometallic approach, some two dozens of further 2,6‐difluoropyridine derivatives were prepared applying a combination of modern organometallic methods such as site selective hydrogen/metal and halogen/metal permutations and deprotonation‐triggered heavy halogen migrations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)