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(2-Pyridyl)sulfonyl Groups for ortho -Directing Palladium- Catalyzed 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) 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.
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https://hal-univ-bourgogne.archives-ouvertes.fr/hal-01671999
Contributeur : Icmub - Université de Bourgogne <>
Soumis le : vendredi 22 décembre 2017 - 18:42:57
Dernière modification le : dimanche 23 juin 2019 - 11:00:03

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Johan Guilbaud, Marine Labonde, Hélène Cattey, Sylvie Contal, Christian Montalbetti, et al.. (2-Pyridyl)sulfonyl Groups for ortho -Directing Palladium- Catalyzed Carbon-Halogen Bond Formation at Functionalized Arenes. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2017, 359 (21), pp.3792 - 3804. ⟨10.1002/adsc.201700858⟩. ⟨hal-01671999⟩

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