6533b7d0fe1ef96bd125a60a
RESEARCH PRODUCT
(2-Pyridyl)sulfonyl Groups for ortho -Directing Palladium- Catalyzed Carbon-Halogen Bond Formation at Functionalized Arenes
Julien RogerJohan GuilbaudNadine PirioChristian MontalbettiSylvie ContalJean-cyrille HiersoJean-cyrille HiersoHélène CatteyMarine Labondesubject
pyridyl sulfonechemistry.chemical_elementelectrophilic fluorinationolefinationphenols010402 general chemistry01 natural sciencesMedicinal chemistryCatalysis[ CHIM.ORGA ] Chemical Sciences/Organic chemistryarene C-H functionalizationhalogenationn-(2-pyridyl)sulfonyl groupOrganic chemistryacidsSulfonylchemistry.chemical_classificationortho-arylationHalogen bond010405 organic chemistryChemistry[CHIM.ORGA]Chemical Sciences/Organic chemistryHalogenationGeneral Chemistryindolespalladiumfluorination0104 chemical sciencesderivativesactivationCarbonprotecting groupPalladiumdescription
International audience; We describe an efficient palladium-catalyzed selective C-H ortho-monohalogenation (X=I, Br, Cl, F) of various functionalized (2-pyridyl) aryl-sulfones. ortho-, meta-and para-functionalization is tolerated at the arene group which undergoes C-H halogenation. Some modifications are also possible on the 2-(arylsulfonyl) heteroaryl directing groups. A comparison of the halogenation efficiency suggests that bromination is the practical method of choice, while chlorination and fluorination are possible but more challenging. Under forcing conditions ortho-dihalogenation can also be achieved.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-10-19 |