Regioflexibility in the functionalization of multiply halogenated quinolines
4-Bromo-6-fluoro-2-(trifluoromethyl)quinoline and 4-bromo-7-fluoro-2-(trifluoromethyl)quinoline were selected as model substrates to explore under what conditions regiochem. exhaustive functionalization reactions can be carried out. This goal was achieved by using trimethylsilyl entities and iodine atoms as the sole auxiliary substituents. The organolithium intermediates could be generated and the protective groups removed without impairing the bromine atom present at the 4-position. [on SciFinder (R)]
WOS:000220048400008
2004
5
1008
1013
CAN 140:375056 27-17 Heterocyclic Compounds (One Hetero Atom) Institut de Chimie moleculaire et biologique,Ecole Polytechnique Federale,Lausanne,Switz. Journal 1434-193X written in English. 31009-33-3; 587885-92-5 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of halogenated quinoline regioisomers using trimethylsilyl protective groups); 685090-71-5P; 685090-72-6P; 685090-74-8P; 685090-75-9P; 685090-76-0P; 685090-78-2P; 685090-79-3P; 685090-81-7P; 685090-82-8P; 685090-84-0P; 685090-85-1P; 685090-87-3P; 685090-88-4P; 685090-89-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of halogenated quinoline regioisomers using trimethylsilyl protective groups); 587886-13-3P; 587886-25-7P; 685090-73-7P; 685090-77-1P; 685090-80-6P; 685090-83-9P; 685090-86-2P; 685090-90-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of halogenated quinoline regioisomers using trimethylsilyl protective groups)
REVIEWED
EPFL