The structural proliferation of 2,6-difluoropyridine through organometallic intermediates
Contrary to a literature claim, 2,6-difluoropyridine-3-carboxaldehyde can be readily prepd. 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 derivs. were prepd. applying a combination of modern organometallic methods such as site selective hydrogen/metal and halogen/metal permutations and deprotonation-triggered heavy halogen migrations. [on SciFinder (R)]
WOS:000220048400010
2004
5
1018
1024
CAN 140:375051 27-16 Heterocyclic Compounds (One Hetero Atom) Institut de Chimie moleculaire et biologique,Ecole Polytechnique Federale,Lausanne,Switz. Journal 1434-193X written in English. 67-64-1 (Acetone); 95-92-1 (Diethyl oxalate); 1513-65-1 (2,6-Difluoropyridine) Role: RCT (Reactant), RACT (Reactant or reagent) (structural proliferation of 2,6-difluoropyridine through organometallic intermediates); 52208-56-7P (3-Chloro-2,6-difluoropyridine); 685517-67-3P; 685517-68-4P; 685517-71-9P; 685517-74-2P; 685517-75-3P; 685517-79-7P; 685517-80-0P; 685517-82-2P; 685517-83-3P; 685517-85-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (structural proliferation of 2,6-difluoropyridine through organometallic intermediates); 80392-79-6P; 88912-23-6P (2,6-Difluoropyridine-4-carboxylic Acid); 155601-65-3P (2,6-Difluoropyridine-3-carboxaldehyde); 171178-50-0P (2,6-Difluoropyridine-3-carboxylic Acid); 193481-62-8P; 193481-63-9P; 209328-85-8P; 685517-69-5P; 685517-70-8P; 685517-72-0P; 685517-73-1P; 685517-76-4P; 685517-77-5P; 685517-78-6P; 685517-81-1P; 685517-84-4P Role: SPN (Synthetic preparation), PREP (Preparation) (structural proliferation of 2,6-difluoropyridine through organometallic intermediates)
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