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Room Temperature Oxidative C−H Functionalization for Selective Construction of Fused Heterocycles by a Low N-Doped Graphitic Carbon/HFIP Catalyst System

66 Pages Posted: 17 Nov 2020 Publication Status: Published

See all articles by He Zhao

He Zhao

South China University of Technology - Key Lab of Functional Molecular Engineering of Guangdong Province

Jialu Sun

South China University of Technology - Key Lab of Functional Molecular Engineering of Guangdong Province

Rongqing Guan

South China University of Technology - Key Lab of Functional Molecular Engineering of Guangdong Province

Qinghao Song

South China University of Technology - Key Lab of Functional Molecular Engineering of Guangdong Province

Huanfeng Jiang

South China University of Technology - Key Lab of Functional Molecular Engineering of Guangdong Province

Min Zhang

South China University of Technology - Key Lab of Functional Molecular Engineering of Guangdong Province

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Abstract

Under metal-free catalysis and external energy input-free conditions, there remain to date significant unmet challenges in precise C−H functionalization with controllable sites and numbers. Here, by establishing a low N-doped hierarchical porous graphitic carbon/hexafluoroisopropanol (HFIP) catalyst system, we demonstrate, for the first time, a direct construction of structurally novel π-extended N,O-heterocycles from tetrahydroquinoxalines and 2-naphthols via selective oxidative aryl C−H bifunctionalization at room temperature, proceeding with the striking features of good substrate and functional group compatibility, excellent step and atom-efficiency, and the use of easily accessible and reusable catalyst and naturally abundant oxidant. Mechanistic study reveals that the in situ formed catalyst-O2 species stabilized by HFIP enables a decent oxidation of substrates to match the coupling processes. The work highlights the potential practicality of the strategy merging suitable carbon material and hexafluoroisopropanol in further development of oxidative C−H functionalization reactions under sustainable catalysis.

Keywords: N-doped graphitic carbon, π-extended N, O-heterocycles, mild C−H functionalization, metal-free and sustainable catalysis

Suggested Citation

Zhao, He and Sun, Jialu and Guan, Rongqing and Song, Qinghao and Jiang, Huanfeng and Zhang, Min, Room Temperature Oxidative C−H Functionalization for Selective Construction of Fused Heterocycles by a Low N-Doped Graphitic Carbon/HFIP Catalyst System. Available at SSRN: https://ssrn.com/abstract=3732385 or http://dx.doi.org/10.2139/ssrn.3732385
This version of the paper has not been formally peer reviewed.

He Zhao

South China University of Technology - Key Lab of Functional Molecular Engineering of Guangdong Province

China

Jialu Sun

South China University of Technology - Key Lab of Functional Molecular Engineering of Guangdong Province

China

Rongqing Guan

South China University of Technology - Key Lab of Functional Molecular Engineering of Guangdong Province ( email )

China

Qinghao Song

South China University of Technology - Key Lab of Functional Molecular Engineering of Guangdong Province ( email )

China

Huanfeng Jiang

South China University of Technology - Key Lab of Functional Molecular Engineering of Guangdong Province ( email )

China

Min Zhang (Contact Author)

South China University of Technology - Key Lab of Functional Molecular Engineering of Guangdong Province ( email )

China