N-(2-pyridyl)sulfonyl groups for ortho-directing palladium carbon-halogen bond formation at functionalized arenes

Abstract We describe an efficient palladium‐catalyzed selective C–H ortho ‐monohalogenation (X=I, Br, Cl, F) of various functionalized (2‐pyridyl)arylsulfones. ortho‐ , meta‐ and para ‐functionalization is tolerated at the arene group which undergoes C–H halogenation. Some modifications are also pos...

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Published inAdvanced synthesis & catalysis Vol. 359; no. 21; pp. 3792 - 3804
Main Authors Guilbaud, Johan, Labonde, Marine, Cattey, Hélène, Contal, Sylvie, Montalbetti, Christian, Pirio, Nadine, Roger, Julien, Hierso, Jean-Cyrille
Format Journal Article
LanguageEnglish
Published Wiley-VCH Verlag 19.10.2017
Subjects
Chemical Sciences
fluorination
palladium
halogenation fluorination pyridylsulfone palladium arene C-H functionalization
halogenation
arene C-H functionalization
pyridylsulfone
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Summary:Abstract We describe an efficient palladium‐catalyzed selective C–H ortho ‐monohalogenation (X=I, Br, Cl, F) of various functionalized (2‐pyridyl)arylsulfones. 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. magnified image
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201700858