Marzi, ElenaBobbio, CarlaCottet, FabriceSchlosser, Manfred2006-03-032006-03-032006-03-03200510.1002/ejoc.200400895https://infoscience.epfl.ch/handle/20.500.14299/227035WOS:0002293636000197007In a model study, 3-fluorophenol and 3-fluoropyridine were converted into all possible regioisomers of the corresponding carboxylic acids by passing through the corresponding organometallic intermediates. As an attempt to generalize the findings reveals, a restricted set of principles and methods suffices to cope with all std. scenarios. The most valuable and versatile tools for the regiochem. exhaustive functionalization of a great variety of substrate patterns are the optionally site-selective metalation (either by reagent/substrate matching or by peripheral coordination control), the use of activating or congesting protective groups and the basicity gradient-driven heavy halogen migration (followed by halogen/metal permutation). [on SciFinder (R)]Carboxylic acids Role: SPN (Synthetic preparation)PREP (Preparation) (arom.; prepn. of all possible regioisomers of (fluoro)(hydroxy)benzoic acid and (fluoro)pyridinecarboxylic acid from m-fluorophenol and m-fluoropyridine); Carboxylation (prepn. of apyridinecarboxylic acid fluoro regioexhaustive prepn; pyridine fluoro regioselective metalation carboxylation; phenol fluoro regioselective metalation carboxylation; benzoic acid hydroxy fluoro regioexhaustive prepntext::journal::journal article::research article