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...
Main Authors: | , , , , , , , , |
---|---|
Other Authors: | |
Format: | Journal Article |
Language: | English |
Published: |
2024
|
Subjects: | |
Online Access: | https://hdl.handle.net/10356/178404 |
_version_ | 1811678139556823040 |
---|---|
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. |
first_indexed | 2024-10-01T02:48:31Z |
format | Journal Article |
id | ntu-10356/178404 |
institution | Nanyang Technological University |
language | English |
last_indexed | 2024-10-01T02:48:31Z |
publishDate | 2024 |
record_format | dspace |
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 |
work_keys_str_mv | AT zhangzhenguo triarylcarbeniumionpairmediatedelectrocatalyticbenzylicchoxygenationinair AT lvyongheng triarylcarbeniumionpairmediatedelectrocatalyticbenzylicchoxygenationinair AT jiliang triarylcarbeniumionpairmediatedelectrocatalyticbenzylicchoxygenationinair AT chenpeng triarylcarbeniumionpairmediatedelectrocatalyticbenzylicchoxygenationinair AT hanshuyan triarylcarbeniumionpairmediatedelectrocatalyticbenzylicchoxygenationinair AT zhuyufei triarylcarbeniumionpairmediatedelectrocatalyticbenzylicchoxygenationinair AT lilanyang triarylcarbeniumionpairmediatedelectrocatalyticbenzylicchoxygenationinair AT jiazhenhua triarylcarbeniumionpairmediatedelectrocatalyticbenzylicchoxygenationinair AT lohteckpeng triarylcarbeniumionpairmediatedelectrocatalyticbenzylicchoxygenationinair |