Ultrahigh Loading Copper Single Atom Catalyst for Palladium-free Wacker Oxidation

doi:10.1007/s40242-022-2130-x

Chemical Research in Chinese Universities ›› 2022, Vol. 38 ›› Issue (5): 1239-1242.doi: 10.1007/s40242-022-2130-x

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Ultrahigh Loading Copper Single Atom Catalyst for Palladium-free Wacker Oxidation

SONG Jingting^1,2, LIU Jia^1,2, LOH Kian Ping^1,2, CHEN Zhongxin¹

1. Department of Chemistry, National University of Singapore, Singapore 117543, Singapore;
2. Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Fuzhou 350207, P. R. China

Received:2022-04-08 Online:2022-10-01 Published:2022-10-08
Contact: CHEN Zhongxin E-mail:chmchz@nus.edu.sg
Supported by:
This work was supported by the National Research Foundation, Prime Minister’s Office, Singapore(No.NRF-CRP16-2015-02).

Abstract

Abstract: Wacker oxidation is an industry-adopted process to transform olefins into value-added epoxides and carbonyls. However, traditional Wacker oxidation involves the use of homogeneous palladium and copper catalysts for the olefin addition and reductive elimination. Here, we demonstrated an ultrahigh loading Cu single atom catalyst(14% Cu, mass fraction) for the palladium-free Wacker oxidation of 4-vinylanisole into the corresponding ketone with N-methylhydroxylamine hydrochloride as an additive under mild conditions. Mechanistic studies by ¹⁸O and deuterium isotope labelling revealed a hydrogen shift mechanism in this palladium-free process using N-methylhydroxylamine hydrochloride as the oxygen source. The reaction scope can be further extended to Kucherov oxidation. Our study paves the way to replace noble metal catalysts in the traditional homogeneous processes with single atom catalysts.

Key words: Single atom catalyst, Wacker oxidation, Ultrahigh loading, High valued chemical, Organic catalysis

SONG Jingting, LIU Jia, LOH Kian Ping, CHEN Zhongxin. Ultrahigh Loading Copper Single Atom Catalyst for Palladium-free Wacker Oxidation[J]. Chemical Research in Chinese Universities, 2022, 38(5): 1239-1242.

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Ultrahigh Loading Copper Single Atom Catalyst for Palladium-free Wacker Oxidation

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