Wiley
Advanced Synthesis and Catalysis
,  volume 365 ,  issue 4 ,  pages 535-543

Site Selective Concerted Nucleophilic Aromatic Substitutions of Azole‐Ligated Diaryliodonium Salts

Publication type: Journal Article
Publication date: 2023-02-02
Wiley
scimago Q1
wos Q1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
Catalysis
Organic Chemistry
Abstract

Diaryliodonium salts are electrophilic arylation reagents in transition metal‐catalyzed and transition metal‐free reaction methods. Herein we present the application of azole‐stabilized diaryliodonium salts with additional thiophene‐2‐yl‐ligands as substrates for metal‐free nucleophilic arylations. Besides their synthesis, we demonstrate their application in chemoselective nitrations, oxygenations, aminations as well as thiolations under umpolung conditions. Convenient one‐pot procedures based on their in situ formation are also discussed.

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4 citations
Postnikov Pavel
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National Research Tomsk Polytechnic University
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"Smart" materials
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N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
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Chemistry of organic and organoelement compounds; chemistry of polymers; production of materials
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GOST Copy
Vlasenko Y. A. et al. Site Selective Concerted Nucleophilic Aromatic Substitutions of Azole‐Ligated Diaryliodonium Salts // Advanced Synthesis and Catalysis. 2023. Vol. 365. No. 4. pp. 535-543.
GOST all authors (up to 50) Copy
Vlasenko Y. A., Kuczmera T. J., Antonkin N. S., Valiev R. R., Postnikov P. S., Nachtsheim B. J. Site Selective Concerted Nucleophilic Aromatic Substitutions of Azole‐Ligated Diaryliodonium Salts // Advanced Synthesis and Catalysis. 2023. Vol. 365. No. 4. pp. 535-543.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1002/adsc.202201001
UR - https://doi.org/10.1002/adsc.202201001
TI - Site Selective Concerted Nucleophilic Aromatic Substitutions of Azole‐Ligated Diaryliodonium Salts
T2 - Advanced Synthesis and Catalysis
AU - Vlasenko, Yulia A
AU - Kuczmera, Thomas J.
AU - Antonkin, Nikita S
AU - Valiev, Rashid R
AU - Postnikov, Pavel S.
AU - Nachtsheim, Boris J
PY - 2023
DA - 2023/02/02
PB - Wiley
SP - 535-543
IS - 4
VL - 365
SN - 1615-4150
SN - 1615-4169
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2023_Vlasenko,
author = {Yulia A Vlasenko and Thomas J. Kuczmera and Nikita S Antonkin and Rashid R Valiev and Pavel S. Postnikov and Boris J Nachtsheim},
title = {Site Selective Concerted Nucleophilic Aromatic Substitutions of Azole‐Ligated Diaryliodonium Salts},
journal = {Advanced Synthesis and Catalysis},
year = {2023},
volume = {365},
publisher = {Wiley},
month = {feb},
url = {https://doi.org/10.1002/adsc.202201001},
number = {4},
pages = {535--543},
doi = {10.1002/adsc.202201001}
}
MLA
Cite this
MLA Copy
Vlasenko, Yulia A., et al. “Site Selective Concerted Nucleophilic Aromatic Substitutions of Azole‐Ligated Diaryliodonium Salts.” Advanced Synthesis and Catalysis, vol. 365, no. 4, Feb. 2023, pp. 535-543. https://doi.org/10.1002/adsc.202201001.