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Palladium-catalyzed carbonylative coupling of pyridine halides with aryl boronic acids

Abstract : The carbonylative Suzuki cross-coupling of a variety of mono-iodopyridines and bromopyridines (1a,b, 3a–c, 5) catalyzed by palladium-phosphane systems has been studied to prepare benzoylpyridine derivatives (2, 4, 6). The selectivity and the rate of the reaction are highly dependent on the reaction conditions, i.e. nature of the palladium catalyst precursor, solvent, temperature and CO pressure. The main side-products arise from direct, non-carbonylative cross-coupling. Under optimized conditions, benzoylpyridines are recovered in high yields (80–95%). The order of reactivity decreases from iodo- to bromopyridines and from 2-, 4- to 3-substituted halopyridines. The reactivity of dihalopyridines has been investigated; 2,6-dibromopyridine (7) and 3,5-dibromopyridine (11) are selectively transformed into either the corresponding benzoyl-phenylpyridine (8, 12) or the corresponding dibenzoylpyridine (9, 13). Dissymmetric 2,5-dihalopyridines (15a,b) are transformed into 2-benzoyl-5-bromopyridine (16) or 2,5-dibenzoylpyridine (17) in high yields. The control of the reaction conditions, i.e. solvent, catalyst precursor, CO pressure, temperature, enables the facile and selective transformation of mono- and dihalopyridines into phenyl pyridyl ketones.
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Samuel Couve-Bonnaire, Jean-François Carpentier, Andre Mortreux, Yves Castanet. Palladium-catalyzed carbonylative coupling of pyridine halides with aryl boronic acids. Tetrahedron, Elsevier, 2003, 59 (16), pp.2793-2799. ⟨10.1016/S0040-4020(03)00342-9⟩. ⟨hal-02384494⟩



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