Publications by Carla Bobbio | EPFL Graph Search

Metalation and derivatization of all six dichlorobenzotrifluorides: Site selectivities

Eric Masson, Fabrice Cottet, Carla Bobbio

The metalation of 2,3-, 2,6-, 2,4- and 3,5-dichlorobenzotrifluorides can be readily effected with std. reagents such as lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, and butyllithium at the chlorine-adjacent 4- and 3-positions and the ch ...

2005

Regiochemically flexible substitutions of di-, tri-, and tetrahalopyridines: the trialkylsilyl trick

Thierry Rausis, Carla Bobbio

2,4-Difluoropyridine, 2,4-dichloropyridine, 2,4,6-trifluoropyridine, 2,4,6-trichloropyridine and 2,3,4,6-tetrafluoropyridine react with std. nucleophiles exclusively at the 4-position under halogen displacement. However, the regioselectivity can be complet ...

2005

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

Fabrice Cottet, Carla Bobbio

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 ...

2005

Removal of fluorine from and introduction of fluorine into polyhalopyridines: an exercise in nucleophilic hetarenic substitution

Thierry Rausis, Carla Bobbio

Starting from six industrially available fluorinated pyridines, an expedient access to all three tetrafluoropyridines, all six trifluoropyridines, and the five non-com. difluoropyridines was developed. The methods employed for the selective removal of fluo ...

2005

Rerouting Nucleophilic Substitution from the 4-Position to the 2- or 6-Position of 2,4-Dihalopyridines and 2,4,6-Trihalopyridines: The Solution to a Long-Standing Problem

Thierry Rausis, Carla Bobbio

2,4-Difluoro-, 2,4,6-trifluoro-, and 2,3,4,6-tetra(fluoro)pyridine undergo nucleophilic substitution preferentially if not exclusively at the 4-position. However, after the introduction of a trialkylsilyl group at C-3 or C-5, the halogen at the 6-(2-)posit ...

2005

Selective Functionalization of 2-Fluoropyridine, 2,3-Difluoropyridine, and 2,5-Difluoropyridine at Each Vacant Position

Carla Bobbio

The concept of "regioexhaustive substitution" has been successfully applied to 2-fluoro-, 2,3-difluoro-, and 2,5-difluoropyridine. All vacant positions were amenable to regioselective metalation and subsequent carboxylation by employing either chlorine as ...

2005

The organometallic approach as a powerful tool for the site selective functionalization of halogenated pyridines

Carla Bobbio

EPFL2003