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Rhodium(III)-Catalyzed Direct Coupling of Quinoline-8-Carbaldehydes with (Het)Arylboronic Acids for the Synthesis of 8‑Aryloylquinolines

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journal contribution
posted on 28.07.2020, 11:35 by Xue-Li Lyu, Shi-Sheng Huang, Yuan-Qiong Huang, Yong-Qiang Li, Hong-Jian Song, Yu-Xiu Liu, Qing-Min Wang
Herein, we describe a method for the synthesis of aryl-(het)­aryl ketones by Rh­(III)-catalyzed direct coupling between quinoline-8-carbaldehydes and (het)­arylboronic acids. The method has a broad substrate scope, a high functional group tolerance, and uses commercially available starting materials. Scale-up of the reaction and subsequent synthesis of tubulin polymerization inhibitor demonstrated its utilities. A plausible mechanism was proposed on the basis of the fact that a stable cycloacylrhodium intermediate complex could be used as catalyst, and the complex reacted stoichiometrically with (het)­arylboronic acids.