Iridium-Catalyzed Synthesis of Substituted Indanones from Aromatic Carboxylates and Unsaturated Ketones
journal contributionposted on 2019-08-06, 14:04 authored by Guodong Zhang, Zhiyong Hu, Giulia Bertoli, Lukas J. Gooßen
A catalytic annulation is presented that provides straightforward, modular synthetic access to 3-substituted indanones from benzoic acids and α,β-unsaturated ketones. It is catalyzed by a bimetallic Ir/In system and proceeds via hydroarylation followed by Claisen condensation and optional retro-Claisen deacylation. The annulation may be combined into a one-pot procedure with the synthesis of the unsaturated ketone substrates from aldehydes and acetone. Two complementary reaction protocols are provided that are applicable to diversely functionalized electron-rich and electron-poor substrates.
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one-pot procedureUnsaturated Ketoneshydroarylationproceedbenzoic acidsannulationSubstituted Indanonesaccessketone substratesClaisen condensationaldehydediversely functionalized electron-richretro-Claisen deacylationelectron-poor substratesAromatic Carboxylatesreaction protocolsbimetallicacetoneindanone3-synthesisIridium-Catalyzed Synthesis