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

Result code in 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>

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10400 - Chemical sciences

Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2025

Confidentiality

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

Name of the periodical

Angewandte Chemie - International Edition

ISSN

1433-7851

e-ISSN

1521-3773

Volume of the periodical

64

Issue of the periodical within the volume

42

Country of publishing house

DE - GERMANY

Number of pages

14

Pages from-to

"e202510715"

UT code for WoS article

001563362200001

EID of the result in the Scopus database

2-s2.0-85216508537