Nikitin, Maksim and Ötvös, Sandor B. and Ghosh, Indrajit and Philipp, Maximilian and Gschwind, Ruth and Kappe, C. Oliver and Koenig, Burkhard (2025) Brønsted Acid-Facilitated Thioetherification Cross-Coupling Reactions with Nickel and Visible Light. ACS CATALYSIS, 15 (3). pp. 1467-1476. ISSN 2155-5435
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Transition metal-catalyzed cross-coupling reactions are essential in modern organic synthesis, facilitating the rapid creation of complex molecular structures. Traditionally, these reactions rely heavily on conventional bases, with only a few exceptions reported. Recently, we developed adaptive dynamic homogeneous catalysis (AD-HoC), a method that enables C(sp2)-S cross-couplings without needing traditional ligands, bases, or additives. Given the growing demand for protocols compatible with acidic conditions in metal-catalyzed cross-couplings, we revisited AD-HoC to pioneer acid-facilitated transition metal-catalyzed thioetherification. Our method enables the swift synthesis of thioethers using nickel and visible light, with a substoichiometric amount of Br & oslash;nsted acid acting as an enabler. NMR kinetic studies indicate that in the absence of acid, the system displays an induction period characteristic of autocatalysis. Introducing the acid as a simple additive eliminates this induction period and significantly accelerates the reaction. Moreover, the protocol has been successfully scaled to gram-level synthesis using continuous flow technology, achieving productivities of over 100 g per hour in a commercially available lab-scale photoreactor. This highlights the method's robustness and scalability, making it a powerful tool for large-scale applications.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | BOND FORMATION; FLOW; PHOTOCHEMISTRY; ILLUMINATION; ARYLATION; HYDROGEN; ARYL; AD-HoC; nickel; visible light; photoredoxcatalysis; Br & oslash;nsted acid; flow chemistry |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 13 Aug 2026 05:03 |
| Last Modified: | 13 Aug 2026 05:03 |
| URI: | https://pred.uni-regensburg.de/id/eprint/66926 |
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