RhIII-Catalyzed C6-Selective Oxidative C?H/C?H Crosscoupling of 2-Pyridones with Thiophenes |
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| Authors: | Gao Huang Yujia Shan Dr Jin-Tao Yu Dr Changduo Pan |
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| Institution: | 1. School of Petrochemical Engineering, Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, Changzhou University, Changzhou, 213164 P. R. China;2. School of Chemical and Environmental Engineering, Jiangsu University of Technology, Changzhou, 213001 P. R. China |
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| Abstract: | 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. |
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| Keywords: | C?H activation dehydrogenative cross-coupling diheteroaryl pyridines rhodium |
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