Takagishi, SadahitoSchlosser, Manfred2006-03-032006-03-032006-03-03199110.1055/s-1991-20650https://infoscience.epfl.ch/handle/20.500.14299/226887At -75 Deg, the superbasic mixt. of BuLi and KOCMe3 metalates 2-, 3-, and 4-FC6H4Me exclusively at an arom. position adjacent to the halogen, as demonstrated by quenching with CO2 to give the corresponding benzoic acids. In contrast, a mixt. of LiN(CHMe2)2 and KOCMe3 selectively deprotonates the benzylic positions of 2- and 3-FC6H4Me to give after quenching with CO2 the corresponding phenylacetic acids. With 3-(F3C)C6H4Me, metal/hydrogen exchange again occurs at the Me group while the corresponding 2- and 4-isomers do not produce interceptable organometallic intermediates. [on SciFinder (R)]Regiochemistry (of metalation of fluoromethylarenes with potassium butoxide-butyllithium or -lithium diisopropylamide); Metalation (regioselectiveof fluoromethylarenes with potassium butoxide-butyllithium or -lithium diisopropylamide)regioselective metalation fluoromethylarene; fluorotoluene regioselective metalation; trifluoromethyltoluene regioselective metalation; arom position site selective metalation; benzylic position site selective metalationtext::journal::journal article::research article