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Regioselective Synthesis of Isocoumarins via Iridium(III)-Catalyzed Oxidative Cyclization of Aromatic Acids with Propargyl Alcohols

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journal contribution
posted on 07.02.2019, 00:00 by Pinki Sihag, Masilamani Jeganmohan
An Ir­(III)-catalyzed oxidative cyclization of benzoic acids with propargyl alcohols to give substituted isocoumarins in a highly regioselective manner is described. This protocol has a broad substrate scope with high functional group tolerance. The observed isocoumarins were converted into biologically active tetracyclic indeno­[2,1-c]­isocoumarins by Lewis acid-mediated cyclization. A possible reaction mechanism is proposed and strongly supported by the detailed mechanistic investigation and DFT.

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