Generalizing Vinyl Halide Cross-Coupling Reactions with Photoredox and Photoredox/Nickel Dual Catalysis

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989100%3A27640%2F25%3A10258709" target="_blank" >RIV/61989100:27640/25:10258709 - isvavai.cz</a>

Výsledek na webu

<a href="https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.202510715" target="_blank" >https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.202510715</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/anie.202510715" target="_blank" >10.1002/anie.202510715</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Generalizing Vinyl Halide Cross-Coupling Reactions with Photoredox and Photoredox/Nickel Dual Catalysis

Popis výsledku v původním jazyce

Reliable, broadly applicable cross-coupling conditions that deliver the desired products with minimal optimization are essential in pharmaceutical research, where efficient synthesis accelerates lead discovery and late-stage diversification. Although advances like high-throughput additive screening and commercial catalyst/ligand libraries improve prediction in specific systems, a general strategy for vinyl halide cross-coupling across diverse bond-forming reactions remains elusive. Herein, we report a general and highly predictable method for vinyl halide cross-coupling under photoredox conditions, employing two complementary catalytic systems. In the first, the organic photocatalyst 4CzIPN enables efficient coupling with nucleophiles such as thiols, selenols, sulfinate salts, activated alkenes, phosphorus (III), and boron compounds, affording C(sp2)&amp; horbar;S, &amp; horbar;Se, &amp; horbar;C, &amp; horbar;P, and &amp; horbar;B bonds in high yields. In the second, a dual nickelphotoredox catalytic system facilitates coupling with less reactive nucleophiles, including phosphorus (V), nitrogen, and oxygen. This approach enables seven distinct bond-forming reactions, offering broad electrophile and nucleophile scope, high functional group tolerance, and applicability to the late-stage functionalization of complex biomolecules. The simple and consistent conditions enable one-pot, two-step bifunctional transformations by sequentially activating distinct chemical bonds involving nucleophiles and electrophiles.

Název v anglickém jazyce

Generalizing Vinyl Halide Cross-Coupling Reactions with Photoredox and Photoredox/Nickel Dual Catalysis

Popis výsledku anglicky

Reliable, broadly applicable cross-coupling conditions that deliver the desired products with minimal optimization are essential in pharmaceutical research, where efficient synthesis accelerates lead discovery and late-stage diversification. Although advances like high-throughput additive screening and commercial catalyst/ligand libraries improve prediction in specific systems, a general strategy for vinyl halide cross-coupling across diverse bond-forming reactions remains elusive. Herein, we report a general and highly predictable method for vinyl halide cross-coupling under photoredox conditions, employing two complementary catalytic systems. In the first, the organic photocatalyst 4CzIPN enables efficient coupling with nucleophiles such as thiols, selenols, sulfinate salts, activated alkenes, phosphorus (III), and boron compounds, affording C(sp2)&amp; horbar;S, &amp; horbar;Se, &amp; horbar;C, &amp; horbar;P, and &amp; horbar;B bonds in high yields. In the second, a dual nickelphotoredox catalytic system facilitates coupling with less reactive nucleophiles, including phosphorus (V), nitrogen, and oxygen. This approach enables seven distinct bond-forming reactions, offering broad electrophile and nucleophile scope, high functional group tolerance, and applicability to the late-stage functionalization of complex biomolecules. The simple and consistent conditions enable one-pot, two-step bifunctional transformations by sequentially activating distinct chemical bonds involving nucleophiles and electrophiles.

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

Angewandte Chemie - International Edition

ISSN

1433-7851

e-ISSN

1521-3773

Svazek periodika

64

Číslo periodika v rámci svazku

42

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

14

Strana od-do

"e202510715"

Kód UT WoS článku

001563362200001

EID výsledku v databázi Scopus

2-s2.0-85216508537