IBS Publications Repository: [4+2] or [4+1] Annulation: Changing the Reaction Pathway of a Rhodium-Catalyzed Process by Tuning the Cp Ligand

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[4+2] or [4+1] Annulation: Changing the Reaction Pathway of a Rhodium-Catalyzed Process by Tuning the Cp Ligand

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Title: [4+2] or [4+1] Annulation: Changing the Reaction Pathway of a Rhodium-Catalyzed Process by Tuning the Cp Ligand

Subject: annulations, ; cyclopentadienyl ligands, ; reaction mechanisms, ; rhodium catalysis

Journal: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.56, no.9, pp.2408 - 2412

Abstract: A change in reaction pathway was achieved for the first time by tuning the cyclopentadienyl (Cp) ligand used for the rhodium-catalyzed cyclization of benzamides with conjugated enynones. Depending on the Cp ligand, the reaction pathway switched between [4+2] and [4+1] annulation. Electronic effects turned out to be crucial for the product distribution. The dichotomy was attributed to the alteration of the Lewis acidity of the resultant Cp-bound rhodium species. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim