Photoredox/Nickel Dual Catalytic C(sp2)-S Cross-coupling of Bromoanilines Enabled by Mineral Acids
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989100%3A27640%2F25%3A10258735" target="_blank" >RIV/61989100:27640/25:10258735 - isvavai.cz</a>
Result on the web
<a href="https://advanced.onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.70026" target="_blank" >https://advanced.onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.70026</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/adsc.70026" target="_blank" >10.1002/adsc.70026</a>
Alternative languages
Result language
angličtina
Original language name
Photoredox/Nickel Dual Catalytic C(sp2)-S Cross-coupling of Bromoanilines Enabled by Mineral Acids
Original language description
Cross-coupling reactions are essential tools in modern organic synthesis, enabling the formation of carbon-heteroatom (C-X) bonds. Despite significant advancements in method development, particularly with palladium, copper, and nickel catalysis, including recent progress in photoredox catalysis, their efficiency is often limited when sensitive functional groups, such as thiols and amines, are present in the nucleophile or electrophile, and typically requires extensive protection-deprotection strategies. Herein, a practical synthetic approach is reported that employs mineral acids as unconventional reagents to facilitate C(sp2)-S cross-coupling between bromoanilines (or other electrophiles bearing free primary amines as functional groups) and thiols, thereby eliminating the need for protecting group manipulations. Additionally, protonation alters the electronic influence of the aniline moiety, transforming it from an electron-donating to an electron-withdrawing group, which promotes oxidative addition, and the acidic medium suppresses polythiolate formation, enhancing nickel catalysts' accessibility and reducing inner filter effects in photocatalysis. This strategy enables efficient and high-yielding synthesis of amino thioethers across a broad substrate scope, underscoring the value of acid-assisted cross-coupling as a streamlined and robust photoredox methodology for C(sp2)-S bond formation.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10400 - Chemical sciences
Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Advanced Synthesis and Catalysis
ISSN
1615-4150
e-ISSN
1615-4169
Volume of the periodical
367
Issue of the periodical within the volume
19
Country of publishing house
DE - GERMANY
Number of pages
7
Pages from-to
"Nestránkováno"
UT code for WoS article
001583318800001
EID of the result in the Scopus database
2-s2.0-105017380659