Copper(I)-photocatalyzed addition of trichloromethanesulfenyl chloride to olefinic compounds

Petek, Nejc (avtor), Zorko, Tilen (avtor), Škrinjar, Martin (avtor), Grošelj, Uroš (avtor), Svete, Jurij (avtor), Kočar, Drago (avtor), Štefane, Bogdan (avtor)

Atom transfer radical addition (ATRA) reactions are essential transformations in organic synthetic chemistry that enable the atom-economic difunctionalization of abundant olefin feedstocks. In this way, a rich chemical space can be opened up by well-planned combinations of simple starting materials. To build an efficient photocatalytic transformation, the reactivity of trichloromethanesulfenyl chloride toward alkenes and alkynes was investigated under photocatalytic Cu(I) reaction conditions. In this study, we found that trichloromethanesulfenyl chloride can be added to a series of olefins (such as styrenes and electron-rich and -poor olefins) in the presence of 1 mol% [Cu(dmp)$_2$]BF$_4$ photocatalyst and blue LED irradiation, producing α-chloro trichloromethylthioethers in good yields. Experimental and theoretical (DFT) mechanistic studies are consistent with the proposed radical chain mechanism of transformation. This study may serve as a valuable reference for the development of new coupling reactions that are economical and highly efficient processes.

• Jezik: Angleški jezik
• Ključne besede: copper photocatalysis, alkenes, sulfenylation, radical chain reaction
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2025
• Št. strani: 8 str.
• Številčenje: Vol. 30, iss. 3, art. 661
• PID: 20.500.12556/RUL-167038
• UDK: 547.1:544.526.5:546.56
• ISSN pri članku: 1420-3049
• DOI: 10.3390/molecules30030661
• COBISS.SI-ID: 225061891
• Datum objave v RUL: 05.02.2025

Gradivo je del revije

• Naslov: Molecules
• Skrajšan naslov: Molecules
• Založnik: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: fotokataliza, alkeni, sulfenil kloridi, radikalske verižne reakcije

Projekti

• Financer: ARIS - Javna agencija za znanstvenoraziskovalno in inovacijsko dejavnost Republike Slovenije
• Številka projekta: P1-0179
• Naslov: Napredna organska sinteza in kataliza