1619224-97-3Relevant academic research and scientific papers
Palladium-Catalyzed C-H Functionalization of Aromatic Oximes: A Strategy for the Synthesis of Isoquinolines
Zhu, Zhongzhi,Tang, Xiaodong,Li, Xianwei,Wu, Wanqing,Deng, Guohua,Jiang, Huanfeng
, p. 1401 - 1409 (2016/03/01)
An efficient strategy for synthesis of isoquinolines via Pd(II)-catalyzed cyclization reaction of oximes with vinyl azides or homocoupling of oximes is reported. Oximes could serve as a directing group and an internal oxidant in the transformation. This reaction features good functional group tolerance and provides a useful protocol for the synthesis of different kinds of isoquinolines under mild conditions. Some control experiments and 15N isotope labeling experiments were conducted for the mechanistic research. (Chemical Equation Presented).
Methyl ketone oxime esters as nucleophilic coupling partners in Pd-catalyzed C-H alkylation and application in the synthesis of isoquinolines
Zhang, Zhi-Wei,Lin, Aijun,Yang, Jiong
, p. 7041 - 7050 (2014/08/18)
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.
