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Multicomponent Synthesis of Isoindolinone Frameworks via Rh III -Catalysed in situ Directing Group-Assisted Tandem Oxidative Olefination/Michael Addition.
Chemistry, An Asian Journal 2018 April 5
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.
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