Green oxidation of indoles using halide catalysis

Green oxidation of indoles using halide catalysis

Oxidation of indoles is a fundamental organic transformation to deliver a variety of synthetically and pharmaceutically valuable nitrogen-containing compounds. Prior methods require the use of either organic oxidants (meta-chloroperoxybenzoic acid, N-bromosuccinimide, t-BuOCl) or stoichiometric toxi...

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Main Authors: Xu, Jun, Liang, Lixin, Zheng, Haohao, Chi, Robin Yonggui, Tong, Rongbiao
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Homogeneous Catalysis
Synthetic Chemistry Methodology
Online Access:https://hdl.handle.net/10356/155119
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1551192023-02-28T19:56:15Z Green oxidation of indoles using halide catalysis Xu, Jun Liang, Lixin Zheng, Haohao Chi, Robin Yonggui Tong, Rongbiao School of Physical and Mathematical Sciences Science::Chemistry Homogeneous Catalysis Synthetic Chemistry Methodology Oxidation of indoles is a fundamental organic transformation to deliver a variety of synthetically and pharmaceutically valuable nitrogen-containing compounds. Prior methods require the use of either organic oxidants (meta-chloroperoxybenzoic acid, N-bromosuccinimide, t-BuOCl) or stoichiometric toxic transition metals [Pb(OAc)4, OsO4, CrO3], which produced oxidant-derived by-products that are harmful to human health, pollute the environment and entail immediate purification. A general catalysis protocol using safer oxidants (H2O2, oxone, O2) is highly desirable. Herein, we report a unified, efficient halide catalysis for three oxidation reactions of indoles using oxone as the terminal oxidant, namely oxidative rearrangement of tetrahydro-β-carbolines, indole oxidation to 2-oxindoles, and Witkop oxidation. This halide catalysis protocol represents a general, green oxidation method and is expected to be used widely due to several advantageous aspects including waste prevention, less hazardous chemical synthesis, and sustainable halide catalysis. Published version This research was financially supported by Research Grant Council of Hong Kong (16311716, 16303617, 16304618) and National Natural Science Foundation of China (21772167). Dr. J.X. also acknowledged the Doctor Start-up Fund ([2018]28) and the Guizhou Province First-Class Disciplines Project (Yiliu Xueke Jianshe Xiangmu-GNYL [2017]008) from Guizhou University of Traditional Chinese Medicine (China). 2022-02-09T06:36:38Z 2022-02-09T06:36:38Z 2019 Journal Article Xu, J., Liang, L., Zheng, H., Chi, R. Y. & Tong, R. (2019). Green oxidation of indoles using halide catalysis. Nature Communications, 10(1), 4754-. https://dx.doi.org/10.1038/s41467-019-12768-4 2041-1723 https://hdl.handle.net/10356/155119 10.1038/s41467-019-12768-4 31628334 2-s2.0-85073603842 1 10 4754 en Nature Communications © 2019 The Author(s). This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/ licenses/by/4.0/. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Homogeneous Catalysis
Synthetic Chemistry Methodology
spellingShingle Science::Chemistry
Homogeneous Catalysis
Synthetic Chemistry Methodology
Xu, Jun
Liang, Lixin
Zheng, Haohao
Chi, Robin Yonggui
Tong, Rongbiao
Green oxidation of indoles using halide catalysis
description Oxidation of indoles is a fundamental organic transformation to deliver a variety of synthetically and pharmaceutically valuable nitrogen-containing compounds. Prior methods require the use of either organic oxidants (meta-chloroperoxybenzoic acid, N-bromosuccinimide, t-BuOCl) or stoichiometric toxic transition metals [Pb(OAc)4, OsO4, CrO3], which produced oxidant-derived by-products that are harmful to human health, pollute the environment and entail immediate purification. A general catalysis protocol using safer oxidants (H2O2, oxone, O2) is highly desirable. Herein, we report a unified, efficient halide catalysis for three oxidation reactions of indoles using oxone as the terminal oxidant, namely oxidative rearrangement of tetrahydro-β-carbolines, indole oxidation to 2-oxindoles, and Witkop oxidation. This halide catalysis protocol represents a general, green oxidation method and is expected to be used widely due to several advantageous aspects including waste prevention, less hazardous chemical synthesis, and sustainable halide catalysis.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Xu, Jun
Liang, Lixin
Zheng, Haohao
Chi, Robin Yonggui
Tong, Rongbiao
format Article
author Xu, Jun
Liang, Lixin
Zheng, Haohao
Chi, Robin Yonggui
Tong, Rongbiao
author_sort Xu, Jun
title Green oxidation of indoles using halide catalysis
title_short Green oxidation of indoles using halide catalysis
title_full Green oxidation of indoles using halide catalysis
title_fullStr Green oxidation of indoles using halide catalysis
title_full_unstemmed Green oxidation of indoles using halide catalysis
title_sort green oxidation of indoles using halide catalysis
publishDate 2022
url https://hdl.handle.net/10356/155119
_version_ 1759853415006994432

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