Photoredox/Nickel Dual Catalytic C(sp2)-S Cross-coupling of Bromoanilines Enabled by Mineral Acids

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Photoredox/Nickel Dual Catalytic C(sp2)-S Cross-coupling of Bromoanilines Enabled by Mineral Acids

Popis výsledku v původním jazyce

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&apos; 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.

Název v anglickém jazyce

Photoredox/Nickel Dual Catalytic C(sp2)-S Cross-coupling of Bromoanilines Enabled by Mineral Acids

Popis výsledku anglicky

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&apos; 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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10400 - Chemical sciences

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Advanced Synthesis and Catalysis

ISSN

1615-4150

e-ISSN

1615-4169

Svazek periodika

367

Číslo periodika v rámci svazku

19

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

7

Strana od-do

"Nestránkováno"

Kód UT WoS článku

001583318800001

EID výsledku v databázi Scopus

2-s2.0-105017380659