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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ligand-Enabled Room-Temperature Three-Component Strategy for Mono-α-arylation of Acetone with Cyclic Diaryliodonium
Naveen Kumar Maurya1,2, Chandra Shekhar Maurya1,2, Malleswara Rao Kuram1,2
1Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, Uttar Pradesh 226031, India.
Abstract:
Selective mono-α-arylation of the simplest ketone, acetone, is a highly sought-after yet challenging transformation. Herein, we present a Pd-catalyzed three-component cascade approach that achieves mono-α-arylation of acetone at room temperature. The ligand was crucial in accomplishing the reaction at room temperature. This methodology enabled a diverse range of difunctionalized biarylated products in good to excellent yields, accomplished by reacting cyclic diaryliodoniums with alkenes and acetone. Mechanistic studies indicate that alkenylation plays a crucial role in α-arylation of acetone, likely stabilizing the Pd complex and enabling the cascade reaction with acetone. A gram-scale reaction and further synthetic manipulations have been demonstrated.
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