1442660-05-0Relevant articles and documents
Oxidative coupling of Michael acceptors with aryl nucleophiles produced through rhodium-catalyzed C-C bond activation
Gregerson, Caroline E.,Trentadue, Kathryn N.,Phipps, Erik J. T.,Kirsch, Janelle K.,Reed, Katherine M.,Dyke, Gabriella D.,Jansen, Jacob H.,Otteman, Christian B.,Stachowski, Jessica L.,Johnson, Jeffrey B.
supporting information, p. 5944 - 5948 (2017/07/25)
Utilizing rhodium catalysis, aryl nucleophiles generated via carbon-carbon single bond activation successfully undergo oxidative coupling with Michael acceptors. The reaction scope encompasses a broad range of nucleophiles generated from quinolinyl ketones as well as a series of electron deficient terminal alkenes, illustrating the broad potential of intersecting carbon-carbon bond activation with synthetically useful coupling methodologies. The demonstrated oxidative coupling produces a range of cinnamyl derivatives, several of which are challenging to prepare via conventional routes.
Catalytic formation of ketones from unactivated esters through rhodium chelation-assisted C-O bond activation
Wang, Jingjing,Zuo, Sujing,Chen, Weiqiang,Zhang, Xinrui,Tan, Kaixin,Tian, Yun,Wang, Jianhui
, p. 8217 - 8231 (2013/09/24)
A new method for building aryl aryl ketones containing heterocyclic rings through chelation-assisted C-O bond activation catalyzed by a rhodium complex has been developed. In this reaction, methyl quinoline-8-carboxylate, methyl quinoxaline-5-carboxylate, and their derivatives were reacted with an excess amount of a substituted phenyl boronic acid in the presence of a rhodium(I) complex to give substituted phenyl(quinolin-8-yl)methanone, phenylquinoxalin-5- ylmethanone, and their derivatives in medium to high yields. The current method offers a highly favorable synthetic pathway to efficiently build related drugs with an 8-benzoylquinoline core structure. This method may prove especially valuable for medicinal chemists for the late-stage introduction of versatile ketone moieties into complex scaffolds for diversity-oriented synthetic strategies.