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- W1970785421 endingPage "7050" @default.
- W1970785421 startingPage "7041" @default.
- W1970785421 abstract "Methyl ketone oxime esters have been found to be excellent coupling partners for C(sp2)–C(sp3) bond formation via Pd-catalyzed aromatic C–H activation. This transformation forms the basis of an approach to regioselectively synthesize substituted isoquinolines via coupling with aryloxime esters. Our mechanistic studies suggested that the reaction proceeded through Pd(II)-catalyzed aromatic C–H activation, tautomerization, and a 1,3-shift of the palladacycle-ligated methyl ketone oxime ester to enable the C–C bond formation by reductive elimination, and intramolecular condensation of an imido-Pd(II) intermediate to form the heterocycle. The aryloxime group not only was used as a directing group for Pd-catalyzed aromatic C–H activation but also functioned as an internal oxidant to allow the reaction to be redox-neutral. Our study illuminated the scope and limitations of this C–H alkylation process, which may serve as the point of departure for developing other C–H functionalization reactions using oxime esters and potentially other carbonyl derivatives as the nucleophilic coupling partners." @default.
- W1970785421 created "2016-06-24" @default.
- W1970785421 creator A5011404596 @default.
- W1970785421 creator A5019005078 @default.
- W1970785421 creator A5091490278 @default.
- W1970785421 date "2014-07-11" @default.
- W1970785421 modified "2023-09-29" @default.
- W1970785421 title "Methyl Ketone Oxime Esters as Nucleophilic Coupling Partners in Pd-Catalyzed C–H Alkylation and Application in the Synthesis of Isoquinolines" @default.
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