Wang Jie, Wang Mingyang, Chen Kehao, Zha Shanke, Song Chao, Zhu Jin
Department of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, Nanjing University , Nanjing 210093, China.
Org Lett. 2016 Mar 4;18(5):1178-81. doi: 10.1021/acs.orglett.6b00310. Epub 2016 Feb 24.
A distinct C-H activation-based traceless synthetic protocol via electrophilic removal of a directing group is reported, complementing the currently exclusively used nucleophilic strategy. Rh(III)-catalyzed, N-nitroso-directed C-H activation allows the development of a traceless, atom- and step-economic, cascade approach for the synthesis of indole skeletons, starting from readily available N-nitroso and α-diazo-β-keto compounds. Importantly, the cyclization/denitrosation reaction represents a hitherto unobserved reactivity pattern for the N-nitroso group.
报道了一种通过亲电去除导向基团基于C-H活化的独特无痕合成方案，它补充了目前唯一使用的亲核策略。铑(III)催化的、N-亚硝基导向的C-H活化使得能够从容易获得的N-亚硝基和α-重氮-β-酮化合物出发，开发一种用于合成吲哚骨架的无痕、原子和步骤经济的级联方法。重要的是，环化/脱亚硝基反应代表了N-亚硝基基团迄今未观察到的反应模式。
