Iridium-Catalyzed Synthesis of Substituted Indanones from Aromatic Carboxylates and Unsaturated Ketones

A catalytic annulation is presented that provides straightforward, modular synthetic access to 3-substituted indanones from benzoic acids and alpha,beta-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.