State Key Laboratory for Oxo Synthesis Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000 (P. R. China).
Graduate University of Chinese Academy of Sciences, Beijing, 100049 (P. R. China).
Chemistry. 2015 Jun 1;21(23):8591-6. doi: 10.1002/chem.201500272. Epub 2015 May 4.
A copper-catalyzed C-C bond cleavage reaction of 1,3-dicarbonyl compounds with 2-iodoanilines was developed. In this process, the ortho effect played an important role in the reactivity and a new reaction pathway that involved a (2-aminophenyl)-bis-(1,3-dicarbonyl) copper species was clearly observed by a time-course HRMS analysis of the reaction mixture. Unlike the previous reports, both the nucleophilic and electrophilic parts of the 1,3-dicarbonyl compound were coupled with 2-iodoaniline by C-C bond cleavage to form o-(N-acylamino)aryl ketones, which could be efficiently converted into multisubstituted indoles.
发展了一种铜催化的 1,3-二羰基化合物与 2-碘苯胺的 C-C 键断裂反应。在这个过程中，邻位效应在反应活性中起着重要作用，通过对反应混合物的时间分辨高分辨质谱分析，清楚地观察到涉及（2-氨基苯基）-双（1,3-二羰基）铜物种的新反应途径。与之前的报道不同，1,3-二羰基化合物的亲核和亲电部分都通过 C-C 键断裂与 2-碘苯胺偶联，形成邻-（N-酰氨基）芳基酮，这些酮可以有效地转化为多取代吲哚。
