Das, Kousik and Saha, Nayan and Li, Zhuofan and Ghosh, Indrajit and König, Burkhard (2025) Generalizing Vinyl Halide Cross-Coupling Reactions with Photoredox and Photoredox/Nickel Dual Catalysis. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 64 (42): e202510715. ISSN 1521-3773
Full text not available from this repository. (Request a copy)Abstract
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)& horbar;S, & horbar;Se, & horbar;C, & horbar;P, and & 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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ALKENYL SULFIDES; AZOLES; ARYL; HETEROARYL; LIGAND; Cross-coupling; General method; Nickel; Photoredox; Vinyl halide |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 23 Sep 2026 04:26 |
| Last Modified: | 23 Sep 2026 04:26 |
| URI: | https://pred.uni-regensburg.de/id/eprint/66549 |
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