14300-16-4Relevant academic research and scientific papers
Intramolecular cooperative C-C bond cleavage reaction of 1,3-dicarbonyl compounds with 2-iodoanilines to give o-(N-Acylamino)aryl ketones and multisubstituted indoles
Xing, Qi,Lv, Hui,Xia, Chungu,Li, Fuwei
, p. 8591 - 8596 (2015/06/02)
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.
Interrupted fischer-indole intermediates via oxyarylation of alkenyl boronic acids
Wang, Heng-Yen,Anderson, Laura L.
, p. 3362 - 3365 (2013/07/26)
The oxyarylation of alkenyl boronic acids with N-arylbenzhydroxamic acids has been achieved under both copper-mediated and copper-catalyzed conditions to provide access to interrupted Fischer-indole intermediates. This transformation is believed to proceed through a copper-promoted C-O bond forming event followed by a [3,3] rearrangement. The scope of the method is described and mechanistic experiments are discussed.
