The construction of C(sp³)–O bond via copper porphyrin catalyzed cross-dehydrogenative coupling reaction: Substituent and electronic effect of the catalysts

Abstract

The push-pull electronic and steric effect of copper porphyrin catalysts on the cross-dehydrogenative coupling (CDC) reaction between the hydroxyl group of phenol substrates and C(sp³)-H bond have been investigated. Results showed that copper porphyrin bearing electron-withdrawing, bulky steric hindrance or heteroatom of pyridyl groups could increase the catalytic activity in the reaction. 5,10,15,20-(tetrakis(4-pyridyl)porphyrin)copper (CuTPyP) was found the best among all tested catalysts. Phenol substrates bearing various functional groups afforded moderate to excellent yields (99%). Significantly, as compared to other tested copper porphyrins, CuTPyP not only exhibited remarkable higher activity but also could shorten the reaction time from 12 to 6 h.

Graphical Abstract

Keywords:

• Copper porphyrin
• cross-dehydrogenative coupling reaction
• electronic effect
• spatial effect

Additional information

Funding

The authors thank the National Natural Science Foundation of China [No. 21671068] and “Dengfeng Plan” High-level Hospital Construction Opening Project of Foshan Fourth People's Hospital [No. FSSYKF-2020012] for the financial support of this work.