School of Petrochemical Engineering, Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, Changzhou University, Changzhou, 213164, P. R. China.
School of Chemical and Environmental Engineering, Jiangsu University of Technology, Changzhou, 213001, P. R. China.
Chemistry. 2021 Aug 25;27(48):12294-12299. doi: 10.1002/chem.202101769. Epub 2021 Jul 13.
A rhodium(III)-catalyzed C6-selective dehydrogenative cross-coupling of 2-pyridones with thiophenes was developed for the synthesis of 6-thiophenyl pyridin-2(1H)-one derivatives. In this reaction, the excellent site selectivity was controlled by the 2-pyridyl directing group on the nitrogen of the pyridone ring. Control experiments indicated that the N-pyridyl was essential for the transformation. To the best of our knowledge, this procedure is the first successful example of the direct C6 heteroarylation of 2-pyridones with electron-rich thiophene derivatives. 4-Pyridone was also used as substrate to generate the corresponding C2 heteroarylated product. Moreover, this pyridyl directing group was readily removable to generate the biheteroaryl structures with a free N-H group.
铑(III)催化的 2-吡啶酮与噻吩的 C6-选择性脱氢交叉偶联反应被开发用于合成 6-噻吩基吡啶-2(1H)-酮衍生物。在该反应中，吡啶酮环上的氮上的 2-吡啶基导向基团控制了优异的位点选择性。控制实验表明，N-吡啶基对于转化是必不可少的。据我们所知，该方法是 2-吡啶酮与富电子噻吩衍生物的直接 C6 杂芳基化的首例成功实例。4-吡啶酮也被用作底物生成相应的 C2 杂芳基化产物。此外，该吡啶基导向基团易于去除，生成具有游离 N-H 基团的双杂芳基结构。
