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Rh(III)‐Catalyzed [3+2] Annulation and C−H Alkenylation of Indoles with 1,3‐Diynes by C−H Activation

Sanjeev Kumar, Saiprasad Nunewar, Khan Mohammad Usama, Vinaykumar Kanchupalli

2021European Journal of Organic Chemistry27 citationsDOI

Abstract

Abstract Described herein is the Rh(III)‐ catalyzed [3+2] annulations and C2‐alkenylations of indoles with 1,3‐diynes, which deliver the synthetically important 3 H ‐pyrrolo[1,2‐ a ]indol‐3‐ones and highly functionalized tetrasubstituted olefin derivatives. Importantly, in this methodology, the additive controlled selective formation of desired scaffolds. This synthetic strategy exhibits high efficiency and broad functional group compatibility. Furthermore, this protocol has been successfully extended to the synthesis of bis‐annulated and trisubstituted alkenes. The method is also smoothly applied for the synthesis of the core structure of protein kinase C inhibitor and melatonin analogues.

Topics & Concepts

ChemistryAnnulationCatalysisCombinatorial chemistryOlefin fiberStereochemistryFunctional groupOrganic chemistryPolymerCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCatalytic Cross-Coupling Reactions
Rh(III)‐Catalyzed [3+2] Annulation and C−H Alkenylation of Indoles with 1,3‐Diynes by C−H Activation | Litcius