Home / Publications / Mild cuprous halide mediated direct C3 monohalogenation of indoles

Mild cuprous halide mediated direct C3 monohalogenation of indoles

Xin He 1
Xin He
, 
Jie Sui 2
Jie Sui
, 
Jikuo Xu 1
Jikuo Xu
, 
Ziyi Wang 1
Ziyi Wang
, 
Tian Yuan 1
Tian Yuan
, 
Di Liu 1
Di Liu
, 
Liang Wang 1
Liang Wang
, 
Qihua Zhu 3
Qihua Zhu
1 School of Chemical and Pharmaceutical Engineering, Changzhou Vocational Institute of Engineering, 213164 Changzhou, P.R. China
2 Nanjing Customs Testing Center for Dangerous Goods and Packaging, 213100 Changzhou, China
3 Department of Medicinal Chemistry, China Pharmaceutical University, 210009 Nanjing, China
10.71267/mencom.7609
Published 2025-02-18
Communication , Volume 35, Issue 2, 214-216
0
Share
Cite this
GOST
 | 
Cite this
GOST Copy
He X. et al. Mild cuprous halide mediated direct C3 monohalogenation of indoles // Mendeleev Communications. 2025. Vol. 35. No. 2. pp. 214-216.
GOST all authors (up to 50) Copy
He X., Sui J., Xu J., Wang Z., Yuan T., Liu D., Wang L., Zhu Q. Mild cuprous halide mediated direct C3 monohalogenation of indoles // Mendeleev Communications. 2025. Vol. 35. No. 2. pp. 214-216.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.71267/mencom.7609
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7609
TI - Mild cuprous halide mediated direct C3 monohalogenation of indoles
T2 - Mendeleev Communications
AU - He, Xin
AU - Sui, Jie
AU - Xu, Jikuo
AU - Wang, Ziyi
AU - Yuan, Tian
AU - Liu, Di
AU - Wang, Liang
AU - Zhu, Qihua
PY - 2025
DA - 2025/02/18
PB - Mendeleev Communications
SP - 214-216
IS - 2
VL - 35
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2025_He,
author = {Xin He and Jie Sui and Jikuo Xu and Ziyi Wang and Tian Yuan and Di Liu and Liang Wang and Qihua Zhu},
title = {Mild cuprous halide mediated direct C3 monohalogenation of indoles},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7609},
number = {2},
pages = {214--216},
doi = {10.71267/mencom.7609}
}
MLA
Cite this
MLA Copy
He, Xin, et al. “Mild cuprous halide mediated direct C3 monohalogenation of indoles.” Mendeleev Communications, vol. 35, no. 2, Feb. 2025, pp. 214-216. https://mendcomm.colab.ws/publications/10.71267/mencom.7609.

Keywords

N-fluorobenzenesulfonimide
cuprous halide
Halogenation
indole derivatives
mild conditions

Abstract

Treatment of indoles with cuprous halide--N-fluorobenzenesulfonimide system in MeCN at room temperature affords the corresponding C3-halogenated derivatives. Cuprous halide acts as a dual-function reagent serving both as the halogen source and the promoter.

References

.
Formal Homo-Nazarov and Other Cyclization Reactions of Activated Cyclopropanes
De Simone F., Saget T., Benfatti F., Almeida S., Waser J.
Chemistry - A European Journal, 2011
.
Synthesis of novel indole derivatives as promising DNA-binding agents and evaluation of antitumor and antitopoisomerase I activities
Lafayette E.A., de Almeida S.M., Cavalcanti Santos R.V., de Oliveira J.F., Amorim C.A., da Silva R.M., Pitta M.G., Pitta I.D., de Moura R.O., de Carvalho Júnior L.B., de Melo Rêgo M.J., de Lima M.D.
European Journal of Medicinal Chemistry, 2017
.
Latest generation of halogen‐containing pesticides
Jeschke P.
Pest Management Science, 2017
.
Anti-Inflammatory Activity and Structure-Activity Relationships of Brominated Indoles from a Marine Mollusc
Ahmad T., Rudd D., Smith J., Kotiw M., Mouatt P., Seymour L., Liu L., Benkendorff K.
Marine Drugs, 2017
.
[b]-Annulated Halogen-Substituted Indoles as Potential DYRK1A Inhibitors
Lechner C., Flaßhoff M., Falke H., Preu L., Loaëc N., Meijer L., Knapp S., Chaikuad A., Kunick C.
Molecules, 2019
.
Synthesis, Characterisation and In Vitro Anticancer Activity of Catalytically Active Indole-Based Half-Sandwich Complexes
Soldevila-Barreda J.J., Fawibe K.B., Azmanova M., Rafols L., Pitto-Barry A., Eke U.B., Barry N.P.
Molecules, 2020
.
Cu–Mn Spinel Oxide Catalyzed Regioselective Halogenation of Phenols and N-Heteroarenes
Singh P.P., Thatikonda T., Kumar K.A., Sawant S.D., Singh B., Sharma A.K., Sharma P.R., Singh D., Vishwakarma R.A.
Journal of Organic Chemistry, 2012
.
Copper-Catalyzed Direct Amidation of Heterocycles with N-Fluorobenzenesulfonimide
Wang S., Ni Z., Huang X., Wang J., Pan Y.
Organic Letters, 2014
.
Palladium-Catalyzed Carbonylation of Indoles for Synthesis of Indol-3-yl Aryl Ketones
Zhao M., Ran L., Chen M., Ren Z., Wang Y., Guan Z.
ACS Catalysis, 2015
.
Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones
Vayer M., Pastor M., Kofink C., Maulide N.
Organic Letters, 2021
.
Palladium-Catalyzed Oxidative Amination of α-Olefins with Indoles
Bhatt S., Wang Y., Pham H.T., Hull K.L.
Organic Letters, 2022
.
A Versatile C-H Halogenation Strategy for Indole Derivatives under Electrochemical Catalyst- and Oxidant-Free Conditions
Sun L., Zhang X., Li Z., Ma J., Zeng Z., Jiang H.
European Journal of Organic Chemistry, 2018
.
A Green and Sustainable Approach for Selective Halogenation of Anilides, Benzanilides, Sulphonamides and Heterocycles †
Lakshmireddy V.M., Naga Veera Y., Reddy T.J., Rao V.J., China Raju B.
Asian Journal of Organic Chemistry, 2019
.
Acylation of indoles via photoredox catalysis: a route to 3-acylindoles
Gu L., Jin C., Liu J., Zhang H., Yuan M., Li G.
Green Chemistry, 2016
.
Regioselective synthesis of 2,3′-biindoles mediated by an NBS-induced homo-coupling of indoles
Huang P., Peng X., Hu D., Liao H., Tang S., Liu L.
Organic and Biomolecular Chemistry, 2017
.
PhI(OAc)2/NaX-mediated halogenation providing access to valuable synthons 3-haloindole derivatives
Himabindu V., Parvathaneni S.P., Rao V.J.
New Journal of Chemistry, 2018
.
Ni–NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics
Bhardwaj N., Singh A.K., Tripathi N., Goel B., Indra A., Jain S.K.
New Journal of Chemistry, 2021
.
DABCO as a practical catalyst for aromatic halogenation with N-halosuccinimides
Xu H., Hu L., Zhu G., Zhu Y., Wang Y., Wu Z., Zi Y., Huang W.
RSC Advances, 2022
.
Cupric Halide Halogenations
Castro C.E., Gaughan E.J., Owsley D.C.
Journal of Organic Chemistry, 1965
.
Controllable transformation of indoles using iodine(iii) reagent
Jian Y., Liang P., Li X., Shao H., Ma X.
Organic and Biomolecular Chemistry, 2023
.
Evolution of a Synthetic Strategy for the Variecolortides
Kuttruff C.A., Mayer P., Trauner D.
European Journal of Organic Chemistry, 2012
.
Electrophilic Bromination of Alkenes, Alkynes, and Aromatic Amines with Iodic Acid/Potassium Bromide Under Mild Conditions
Khazaei A., Zolfigol M.A., Kolvari E., Koukabi N., Soltani H., Bayani L.S.
Synthetic Communications, 2010
.
Rapid Oxidation Indoles into 2‐Oxindoles Mediated by PIFA in Combination with n ‐Bu 4 NCl ⋅ H 2 O
Liang P., Zhao H., Zhou T., Zeng K., Jiao W., Pan Y., Liu Y., Fang D., Ma X., Shao H.
Advanced Synthesis and Catalysis, 2021
.
Green Halogenation of Indoles with Oxone–Halide
Zheng T., Xu J., Cheng S., Ye J., Ma S., Tong R.
Journal of Organic Chemistry, 2023