Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide
Guodong Zhao
1, 2, 3, 4, 5, 6, 7
,
Lixin Liang
2, 6, 7, 8, 9
,
Eryu Wang
2, 6, 7, 8, 9
,
Shaoyan Lou
1, 3, 4, 5, 6
,
Rui Qi
1, 3, 4, 5, 6
,
Rong-Biao Tong
2, 6, 7, 8, 9, 10, 11, 12
3
School of Chinese Pharmacy
5
Beijing 102488
|
6
CHINA
|
7
DEPARTMENT OF CHEMISTRY
9
Kowloon
|
12
Hong Kong Branch of the Guangdong Southern Marine Science and Engineering Laboratory (Guangzhou)
Publication type: Journal Article
Publication date: 2021-03-09
scimago Q1
wos Q1
SJR: 1.928
CiteScore: 16.1
Impact factor: 9.2
ISSN: 14639262, 14639270
Environmental Chemistry
Pollution
Abstract
Oxidative rearrangement of indoles is an important transformation to yield 2-oxindoles and spirooxindoles, which are present in many pharmaceutical agents and bioactive natural products. Previous oxidation methods show either broad applicability or greenness but rarely achieve both. Reported is the discovery of Fenton chemistry-enabled green catalytic oxidative rearrangement of indoles, which has wide substrate scope (42 examples) and greenness (water as the only stoichiometric byproduct) at the same time. Detailed mechanistic studies revealed that the Fenton chemistry generated hydroxyl radicals that further oxidize bromide to reactive brominating species (RBS: bromine or hypobromous acid). This in situ generated RBS is the real catalyst for the oxidative rearrangement. Importantly, the RBS is generated under neutral conditions, which addresses a long-lasting problem of many haloperoxidase mimics that require a strong acid for the oxidation of bromide with hydrogen peroxide. It is expected that this new catalytic Fenton-halide system will find wide applications in organic synthesis.
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55
Total citations:
55
Citations from 2025:
14
(25.46%)
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GOST
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Zhao G. et al. Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide // Green Chemistry. 2021. Vol. 23. No. 6. pp. 2300-2307.
GOST all authors (up to 50)
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Zhao G., Liang L., Wang E., Lou S., Qi R., Tong R. Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide // Green Chemistry. 2021. Vol. 23. No. 6. pp. 2300-2307.
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RIS
Copy
TY - JOUR
DO - 10.1039/d1gc00297j
UR - https://xlink.rsc.org/?DOI=D1GC00297J
TI - Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide
T2 - Green Chemistry
AU - Zhao, Guodong
AU - Liang, Lixin
AU - Wang, Eryu
AU - Lou, Shaoyan
AU - Qi, Rui
AU - Tong, Rong-Biao
PY - 2021
DA - 2021/03/09
PB - Royal Society of Chemistry (RSC)
SP - 2300-2307
IS - 6
VL - 23
SN - 1463-9262
SN - 1463-9270
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2021_Zhao,
author = {Guodong Zhao and Lixin Liang and Eryu Wang and Shaoyan Lou and Rui Qi and Rong-Biao Tong},
title = {Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide},
journal = {Green Chemistry},
year = {2021},
volume = {23},
publisher = {Royal Society of Chemistry (RSC)},
month = {mar},
url = {https://xlink.rsc.org/?DOI=D1GC00297J},
number = {6},
pages = {2300--2307},
doi = {10.1039/d1gc00297j}
}
Cite this
MLA
Copy
Zhao, Guodong, et al. “Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide.” Green Chemistry, vol. 23, no. 6, Mar. 2021, pp. 2300-2307. https://xlink.rsc.org/?DOI=D1GC00297J.