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Direct access to 2-(hetero)arylated pyridines from 6-substituted 2-bromopyridines via phosphine-free palladium-catalyzed C-H bond arylations: the importance of the C6 substituent

Abstract : A phosphine-free palladium catalytic system was found to be very active to promote C-H bond activation/arylation of 5-membered ring heterocycles or electron-deficient arenes with 6-substituted 2-bromopyridines, providing a general, straightforward and environmentally benign synthetic approach to a broad variety of 2-(hetero)arylpyridines. The reactivity of 2-bromopyridines is strongly dependent on the substituent at the C6 position. Several C6 substituents such as Br, CF3, CH3, CHO, or morpholine have been employed. Moreover, the use of 2,6-dibromopyridine as the coupling partner allowed the synthesis in high yields of sym. and unsym. 2,6-di(hetero)arylpyridines, as well as 2-heteroarylpyridines after the C-Br bond cleavage.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01274110
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Submitted on : Monday, February 15, 2016 - 2:07:13 PM
Last modification on : Wednesday, October 28, 2020 - 9:52:04 AM

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Wided Hagui, Neji Besbes, Ezzeddine Srasra, Jean-François Soulé, Henri Doucet. Direct access to 2-(hetero)arylated pyridines from 6-substituted 2-bromopyridines via phosphine-free palladium-catalyzed C-H bond arylations: the importance of the C6 substituent. RSC Advances, Royal Society of Chemistry, 2016, 6 (16), pp.17110-17117. ⟨10.1039/C6RA01861K⟩. ⟨hal-01274110⟩

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