Triaryl carbenium ion pair mediated electrocatalytic benzylic C-H oxygenation in air

The 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 ty...

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Main Authors: Zhang, Zhenguo, Lv, Yongheng, Ji, Liang, Chen, Peng, Han, Shuyan, Zhu, Yufei, Li, Lanyang, Jia, Zhenhua, Loh, Teck-Peng
Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
Format: Journal Article
Language:English
Published: 2024
Subjects:
Online Access:https://hdl.handle.net/10356/178404
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author Zhang, Zhenguo
Lv, Yongheng
Ji, Liang
Chen, Peng
Han, Shuyan
Zhu, Yufei
Li, Lanyang
Jia, Zhenhua
Loh, Teck-Peng
author2 School of Chemistry, Chemical Engineering and Biotechnology
author_facet School of Chemistry, Chemical Engineering and Biotechnology
Zhang, Zhenguo
Lv, Yongheng
Ji, Liang
Chen, Peng
Han, Shuyan
Zhu, Yufei
Li, Lanyang
Jia, Zhenhua
Loh, Teck-Peng
author_sort Zhang, Zhenguo
collection NTU
description The 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.
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spelling ntu-10356/1784042024-06-21T15:31:41Z Triaryl carbenium ion pair mediated electrocatalytic benzylic C-H oxygenation in air Zhang, Zhenguo Lv, Yongheng Ji, Liang Chen, Peng Han, Shuyan Zhu, Yufei Li, Lanyang Jia, Zhenhua Loh, Teck-Peng School of Chemistry, Chemical Engineering and Biotechnology Chemistry Ion pair Triaryl carbenium The 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. Agency for Science, Technology and Research (A*STAR) Nanyang Technological University Submitted/Accepted version We gratefully acknowledge the financial support from Distinguished University Professor grant (Nanyang Technological University); and the Agency for Science, Technology, and Research (A*STAR) under its MTC Individual Research grant (M21K2c0114) and RIE2025 MTC Programmatic Fund (M22K9b0049) for T.-P. L. 2024-06-18T06:29:00Z 2024-06-18T06:29:00Z 2024 Journal Article Zhang, Z., Lv, Y., Ji, L., Chen, P., Han, S., Zhu, Y., Li, L., Jia, Z. & Loh, T. (2024). Triaryl carbenium ion pair mediated electrocatalytic benzylic C-H oxygenation in air. Accounts of Chemical Research. https://dx.doi.org/10.1002/ange.202406588 0001-4842 https://hdl.handle.net/10356/178404 10.1002/ange.202406588 en M21K2c0114 M22K9b0049 Accounts of Chemical Research © 2024 Wiley-VCH GmbH. All rights reserved. This article may be downloaded for personal use only. Any other use requires prior permission of the copyright holder. The Version of Record is available online at http://doi.org/10.1002/ange.202406588. application/pdf
spellingShingle Chemistry
Ion pair
Triaryl carbenium
Zhang, Zhenguo
Lv, Yongheng
Ji, Liang
Chen, Peng
Han, Shuyan
Zhu, Yufei
Li, Lanyang
Jia, Zhenhua
Loh, Teck-Peng
Triaryl carbenium ion pair mediated electrocatalytic benzylic C-H oxygenation in air
title Triaryl carbenium ion pair mediated electrocatalytic benzylic C-H oxygenation in air
title_full Triaryl carbenium ion pair mediated electrocatalytic benzylic C-H oxygenation in air
title_fullStr Triaryl carbenium ion pair mediated electrocatalytic benzylic C-H oxygenation in air
title_full_unstemmed Triaryl carbenium ion pair mediated electrocatalytic benzylic C-H oxygenation in air
title_short Triaryl carbenium ion pair mediated electrocatalytic benzylic C-H oxygenation in air
title_sort triaryl carbenium ion pair mediated electrocatalytic benzylic c h oxygenation in air
topic Chemistry
Ion pair
Triaryl carbenium
url https://hdl.handle.net/10356/178404
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