Palladium-catalyzed N-arylation of sulfoximines with aryl bromides and aryl iodides |
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Authors: | Bolm Hildebrand |
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Affiliation: | Institut fur Organische Chemie der RWTH Aachen, Prof. -Pirlet-Strasse 1, D-52056 Aachen, Germany. |
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Abstract: | Various N-arylated sulfoximines have been synthesized in high yield by a direct approach which is based on a palladium-catalyzed cross-coupling strategy. Aryl bromides of variable substitution pattern were found to be the most effective coupling partners, whereas aryl iodides showed a nonpredictable behavior requiring lithium or silver salts as additives to ensure product formation in acceptable yields. Coupling of (S)-2-(2'-bromophenyl)-4-tert-butyloxazoline with enantiomerically pure (-)-(RS)-S-methyl-S-phenylsulfoximine afforded the corresponding product in good yield as a single diastereomer, showing that the palladium-catalyzed arylation proceeds in a stereospecific manner. The reaction with dibromobenzenes yielded the monosulfonimidoyl arenes in all cases, suggesting that the introduction of the sulfonimidoyl moiety deactivates the arene, thus preventing a second coupling step. |
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