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Multicomponent Synthesis of Isoindolinone Frameworks via RhIII‐Catalysed in situ Directing Group‐Assisted Tandem Oxidative Olefination/Michael Addition |
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| Authors: | Dr Liang Wang Xi Liu Dr Jian‐biao Liu Jun Shen Prof Qun Chen Prof Ming‐yang He |
| Institution: | 1. School of Petrochemical Engineering, Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, Changzhou University, Changzhou, P. R. China;2. College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for, Chemical Imaging in Universities of Shandong, Institute of Molecular, and Nano Science, Shandong Normal University, Jinan, P. R. China |
| Abstract: | A RhIII‐catalysed three‐component synthesis of isoindolinone frameworks via direct assembly of benzoyl chlorides, o‐aminophenols and activated alkenes has been developed. The process involves in situ generation of o‐aminophenol (OAP)‐based bidentate directing group (DG), RhIII‐catalysed tandem ortho C?H olefination and subsequent cyclization via aza‐Michael addition. This protocol exhibits good chemoselectivity and functional group tolerance. Computational studies showed that the presence of hydroxyl group on the N‐aryl ring could enhance the chemoselectivity of the reaction. |
| Keywords: | C− H activation chemoselectivity isoindolinones multicomponent synthesis rhodium |