Converting core compounds into building blocks: The concept of regiochemically exhaustive functionalization

In 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)]


Published in:
European Journal of Organic Chemistry, 10, 2116-2123
Year:
2005
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Note:
CAN 143:153263 27-16 Heterocyclic Compounds (One Hetero Atom) Institute of Chemical Sciences and Engineering (ISIC, BCh),Ecole Polytechnique Federale,Lausanne,Switz. Journal 1434-193X written in English. 860296-19-1P Role: BYP (Byproduct), PREP (Preparation) (prepn. of all possible regioisomers of (fluoro)(hydroxy)benzoic acid and (fluoro)pyridinecarboxylic acid from m-fluorophenol and m-fluoropyridine); 372-20-3 (3-Fluorophenol); 372-47-4 (3-Fluoropyridine); 126940-10-1 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of all possible regioisomers of (fluoro)(hydroxy)benzoic acid and (fluoro)pyridinecarboxylic acid from m-fluorophenol and m-fluoropyridine); 2546-56-7P (4-Chloro-3-fluoropyridine); 87674-09-7P; 146746-69-2P; 860296-13-5P; 860296-14-6P; 860296-15-7P; 860296-16-8P; 860296-17-9P; 860296-18-0P; 860296-20-4P; 860296-21-5P; 860296-22-6P; 860296-23-7P; 860296-24-8P; 860296-25-9P; 860296-26-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of all possible regioisomers of (fluoro)(hydroxy)benzoic acid and (fluoro)pyridinecarboxylic acid from m-fluorophenol and m-fluoropyridine); 345-29-9P (4-Fluoro-2-hydroxybenzoic acid); 393-53-3P (3-Fluoro-4-pyridinecarboxylic acid); 402-66-4P (5-Fluoro-3-pyridinecarboxylic acid); 65145-13-3P (2-Fluoro-4-hydroxybenzoic acid); 67531-86-6P (2-Fluoro-6-hydroxybenzoic acid); 107504-08-5P (5-Fluoro-2-pyridinecarboxylic acid); 152126-31-3P (3-Fluoro-2-pyridinecarboxylic acid); 860296-12-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of all possible regioisomers of (fluoro)(hydroxy)benzoic acid and (fluoro)pyridinecarboxylic acid from m-fluorophenol and m-fluoropyridine)
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 Record created 2006-03-03, last modified 2018-01-27


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