Triaryl Carbenium Ion Pair Mediated Electrocatalytic Benzylic C−H Oxygenation in Air

Author:

Zhang Zhenguo12,Lv Yongheng3,Ji Liang3,Chen Peng1,Han Shuyan1,Zhu Yufei1,Li Lanyang3,Jia Zhenhua123ORCID,Loh Teck‐Peng123ORCID

Affiliation:

1. Henan University of Technology 100 Lianhua Street, Zhongyuan District Zhengzhou 450001 China

2. Division of Chemistry and Biological Chemistry School of Chemistry Chemical Engineering & Biotechnology Nanyang Technological University 21 Nanyang Link Nanyang 637371 Singapore

3. School of Chemistry and Molecular Engineering Nanjing Tech University Nanjing 211816 China

Abstract

AbstractThe selective oxidation of benzylic C−H bonds is a pivotal transformation in organic synthesis. Undoubtedly, achieving efficient and highly selective aerobic oxidation of methylarenes to benzaldehydes has been highly challenging due to the propensity of benzaldehyde to undergo overoxidation under typical aerobic conditions. Herein, we propose an innovative approach to address this issue by leveraging electrocatalytic processes, facilitated by ion‐pair mediators [Ph3C]+[B(C6F5)4]. By harnessing the power of electrochemistry, we successfully demonstrated the effectiveness of our strategy, which enables the selective oxidation of benzylic C−H bonds in benzylic molecules and toluene derivatives. Notably, our approach exhibited high efficiency, excellent selectivity, and compatibility with various functional groups, underscoring the broad applicability of our methodology.

Funder

Missouri Technology Corporation

Publisher

Wiley

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