Department of Chemistry & Biochemistry , Northern Kentucky University , Nunn Drive , Highland Heights , Kentucky 41099 , United States.
Department of Chemistry , The University of Texas Rio Grande Valley , Edinburg , Texas 78541 , United States.
J Org Chem. 2019 Jun 21;84(12):7652-7663. doi: 10.1021/acs.joc.9b00446. Epub 2019 May 1.
Heteroaryl compounds are valuable building blocks in medicinal chemistry and chemical industry. A palladium-catalyzed direct α-C(sp3) heteroarylation of ketones under microwave irradiation is developed and reported in this study. Under optimized conditions, twenty-eight (28) heteroarylated ketones were prepared in this study to demonstrate the substrate scope of this reaction. The ground-state optimized structure of Pd(0) active catalyst with 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) in toluene, and the products of its reaction with 3-bromopyridine and acetophenone were studied using all-atom density functional theory. This study provided insightful information for palladium catalytic system design to generate heteroaryl compounds.
杂芳族化合物是药物化学和化学工业中非常有价值的构建模块。本研究开发并报道了在微波辐射下钯催化的酮的直接α-C(sp3)杂芳基化反应。在优化条件下，本研究制备了二十八（28）种杂芳基酮，以证明该反应的底物范围。使用全原子密度泛函理论研究了钯（0）活性催化剂与 2-二环己基膦-2'，4'，6'-三异丙基联苯（XPhos）在甲苯中的基态优化结构，以及其与 3-溴吡啶和苯乙酮反应的产物。该研究为钯催化体系设计生成杂芳族化合物提供了有见地的信息。
