860296-17-9Relevant academic research and scientific papers
Converting core compounds into building blocks: The concept of regiochemically exhaustive functionalization
Marzi, Elena,Bobbio, Carla,Cottet, Fabrice,Schlosser, Manfred
, p. 2116 - 2123 (2007/10/03)
In a model study, 3-fluorophenol and 3-fluoropyridine were converted into the each time four possible 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 standard scenarios. The most valuable and versatile tools for the regiochemically 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). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
