Palladium-Catalyzed C8-Selective C–H Arylation of Quinoline N-Oxides: Insights into the Electronic, Steric, and Solvation Effects on the Site Selectivity by Mechanistic …

…, TA Ateşin, G Chavez, HD Arman, OV Larionov

Index: Larionov, Oleg V.; Stephens, David; Mfuh, Adelphe M.; Arman, Hadi D.; Naumova, Anastasia S.; Chavez, Gabriel; Skenderi, Behije Organic and Biomolecular Chemistry, 2014 , vol. 12, # 19 p. 3026 - 3036

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Citation Number: 26

Abstract

We report herein a palladium-catalyzed C–H arylation of quinoline N-oxides that proceeds with high selectivity in favor of the C8 isomer. This site selectivity is unusual for palladium, since all of the hitherto described methods of palladium-catalyzed C–H functionalization of quinoline N-oxides are highly C2 selective. The reaction exhibits a broad synthetic scope with respect to quinoline N-oxides and iodoarenes and can be significantly accelerated to ...