Synergistic N-Heterocyclic Carbene/Palladium-Catalyzed Umpolung 1,4-Addition of Aryl Iodides to Enals.

By Wenjun Yang, Bo Ling, Bowen Hu, Haolin Yin, Jianyou Mao, P. Walsh. Angewandte Chemie, 2019

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A (terpy)Pd/NHC cooperative catalyzed umpolung 1,4-addition of aryl iodides to enals to generate various bioactive β,β-diaryl propanoate derivatives is described. The system developed herein not only represents the first palladium-catalyzed arylation of NHC-bound homoenolates but also expands the scope of NHC-induced umpolung transformations. A diverse array of functional groups such as esters, nitriles, alcohols and heterocycles are tolerated under the mild conditions. This protocol also circumvents use of moisture-sensitive organometallic reagents.

Subfields: Organic Chemistry

View Paper: https://www.semanticscholar.org/paper/e492c4a950fb139229e6be4b19d414374b721cb3