Large-scale preparation of aromatic fluorides via electrophilic fluorination with functionalized aryl- or heteroarylmagnesium reagents
Functionalized aryl- or heteroarylmagnesium reagents, prepared from the corresponding bromides or iodides using halogen-magnesium exchange or direct magnesium insertion in the presence of lithium chloride, reacted smoothly with N-fluorobenzenesulfonimide, (PhSO2)2NF, in the mixed solvent (4:1 CH2Cl2-perfluorodecalin) to give the corresponding aromatic fluorides in moderate to good yields. Georg Thieme Verlag Stuttgart · New York.
Yamada, Shigeyuki,Knochel, Paul
experimental part
p. 2490 - 2494
(2010/09/04)
Convenient electrophilic fluorination of functionalized aryl and heteroaryl magnesium reagents
"Chemical Equation Presented" Cive me an "F": Electrophilic fluorination of various aromatic and heteroaromatic Grignard reagents is smoothly performed with (PhSO2)2NF as fluorinating agent in a 4:1 mixture of CH2Cl2/ perfluorodecalin (see scheme). This solvent system allows minimization of most side reactions.
Yamada, Shigeyuki,Gavryushin, Andrei,Knochel, Paul
supporting information; experimental part
p. 2215 - 2218
(2010/06/19)
Thiazole-4-carboxyamide derivatives
The present invention is concerned with novel thiazole 4-carboxyamide derivatives of the general formula (I) and with methods for the preparation thereof, which compounds are useful as metabotropic glutamate receptor antagonists: wherein R1 to R4 are as defined in the specification.
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Page/Page column 56
(2008/06/13)
Pyridine-2-carboxyamide derivatives
The invention relates to compounds of formula I: wherein R1 to R3 are as defined in the specification, to processes for their preparation, to pharmaceutical compositions containing them, and to methods for treating CNS disorders.
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Page/Page column 21
(2008/06/13)
HOMOTRANSMETALLATION DES HALOGENO-3 PYRIDINES BROMEES EN -2 OU -4 PAR LE N-BUTYLLITHIUM. PROPOSITION D'UN NOUVEAU MECANISME DE TELESUBSTITUTION DU BROME.
These are new examples of the homotransmetallation reaction.Instead of the ordinary bromo-metal exchange it is possible to obtain selectively from the 2-bromo 3-fluoro or 2-bromo 3-chloro pyridines the 2-bromo 3-halogeno 4-lithio pyridines, which is very interesting for synthetic utility.From the 4-bromo 3-halogeno pyridines, we can see an isomerization with an halogen dance mechanism and we obtain the 5-bromo 3-halogeno 4-lithio pyridines.In the case of the 2-bromo 3-fluoro pyridine we explain a telesubstitution of bromine from 2 to 4 by a transitory homotransmetallation reaction during the Li-Br exchange.