A Three‐Component Arene Difunctionalization: Merger of C(sp3)/(sp2)−H Bond Addition

Author:

Ghosh Arghadip1ORCID,Kondalarao Koneti1ORCID,Saha Arijit1ORCID,Gandon Vincent2ORCID,Sahoo Akhila K.1ORCID

Affiliation:

1. School of Chemistry University of Hyderabad 500046 Hyderabad Telangana India

2. Institut de Chimie Moléculaire et des Matériaux d'Orsay CNRS UMR 8182 Université Paris-Saclay Bâtiment Henri Moissan, 17 avenue des Sciences 91400 Orsay France

Abstract

AbstractA tandem three‐component C−H bond addition involving the activation of an inert C(sp3)−H bond is reported. The process enables the direct regioselective synthesis of 1,2‐difunctionalized arenes with the formation of C(sp3)− and C(sp2)−C(arene) bonds. 2‐Iodobenzoic acid derivatives behave as masked bifunctional reagent (BFR) and react with 2‐pyridyl‐methyl sulfoximine (MPyS) protected aliphatic acids bearing α,α‐disubstituted groups, and alkenes to produce β‐aryl‐δ‐alkenyl amide derivatives in a single operation. The transformation involves Pd(II)/Pd(IV) and Pd(II)/Pd(0) catalytic systems. Detailed mechanistic studies, including density functional theory (DFT) calculations, reveal the formation of large T‐shaped palladacycles and the onset of a 1,2‐palladium migration via decarboxylation.

Publisher

Wiley

Subject

General Medicine

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