Catalyst- and Oxidizing Reagent-Free Electrochemical Benzylic C(sp3)-H Oxidation of Phenol Derivatives

Zhong-Wei Hou; Ming-Ming Zhang; Wen-Chao Yang; Lei Wang

doi:10.1021/acs.joc.2c00455

Catalyst- and Oxidizing Reagent-Free Electrochemical Benzylic C(sp³)-H Oxidation of Phenol Derivatives

J Org Chem. 2022 Jun 17;87(12):7806-7817. doi: 10.1021/acs.joc.2c00455. Epub 2022 Jun 1.

Authors

Zhong-Wei Hou¹, Ming-Ming Zhang², Wen-Chao Yang², Lei Wang^{1

3}

Affiliations

¹ Advanced Research Institute and Department of Chemistry, Taizhou University, Jiaojiang, Zhejiang, Taizhou 318000, P. R. China.
² Guangling College and School of Horticulture and Plant Protection, Yangzhou University, Jiangsu, Yangzhou 225009, P. R. China.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R. China.

PMID: 35648817
DOI: 10.1021/acs.joc.2c00455

Abstract

A site-selective electrochemical approach for the benzylic C(sp³)-H oxidation reaction of phenol derivatives along with hydrogen evolution has been developed. The protocol proceeds in an easily available undivided cell at room temperature under catalyst- and oxidizing reagent-free conditions. The corresponding aryl aldehydes and ketones are obtained in satisfactory yields, and the gram-scale synthesis is easy to be carried out.