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

Wenjun Yanga, Bo Linga, Bowen Hub, Haolin Yinb, Jianyou Mao,*,a and Patrick J. Walsh*,b

a Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing 211816, China

b Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104, USA

Abstract: 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 NHCinduced 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.

Angewandte Chemie-International Edition 2019 Accepted (2018年影响因子: 12.102).

论文链接：https://onlinelibrary.wiley.com/doi/10.1002/anie.201912584