Oxidation of N-trifluoromethylthio sulfoximines using NaOCl▫$\cdot$▫5▫$H_2O$▫

Testen, Žan (avtor), Jereb, Marjan (avtor)

N-Trifluoromethylthio sulfoximines are biologically interesting compounds, but their potential is still poorly understood. The oxidation of N-trifluoromethylthio sulfoximines led to their corresponding sulfoxide derivatives as a new class of compounds, when using sodium hypochlorite pentahydrate (NaOCl·5H$_2$O) as a green and relatively unexplored reagent. The reactions took place with a small excess of oxidant under environmentally friendly conditions in EtOAc for 16 h at room temperature. Noteworthy distinctions of this transformation are the simplicity, high selectivity, energy and cost efficiency, minimal amounts of non-hazardous waste, isolation of most of the products without the additional need for chromatographic purification, and simple scalability to gram reactions without deterioration of the yield. The reaction exhibited excellent green chemistry metrics with high atom economy (82.0%), actual atom economy (79.5%), reaction mass efficiency (79.7%), E-factor (16.48) and a very high EcoScale score (84.5). Competitive experiments demonstrated that electron-rich substrates are more reactive than their electron-poor counterparts. Furthermore, the Suzuki–Miyaura functionalization of N-trifluoromethylsulfaneylidene sulfoximine could be achieved depending on the conditions, resulting in coupling products with or without an introduced sulfoxide moiety. Sonogashira coupling of N-trifluoromethylsulfaneylidene sulfoximine furnished the expected acetylene derivative in high yield, and the reaction conditions are compatible with the newly introduced sulfaneylidene functionality. Bromine and nickel catalysts were also shown to be deprotecting agents of the sulfoxide group. A selected N-trifluoromethylsulfaneylidene sulfoximine demonstrated its stability in water in the presence of air and in dilute hydrochloric acid, while it converted back to the parent sulfoximine under basic conditions.

• Jezik: Angleški jezik
• Ključne besede: trifluoromethylthio sulfoximines, oxidation, green chemistry, sodium hypochlorite pentahydrate
• 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: 2024
• Št. strani: Str. 2012-2020
• Številčenje: Vol. 22, iss. 10
• PID: 20.500.12556/RUL-160078
• UDK: 547.415.3:542.943
• ISSN pri članku: 1477-0539
• DOI: 10.1039/d3ob02033a
• COBISS.SI-ID: 188149507
• Datum objave v RUL: 16.08.2024

Gradivo je del revije

• Naslov: Organic & biomolecular chemistry
• Skrajšan naslov: Org. biomol. chem.
• Založnik: Royal Society of Chemistry
• ISSN: 1477-0539
• COBISS.SI-ID: 19836967

Licence

• Licenca: CC BY 3.0, Creative Commons Priznanje avtorstva 3.0 Nedoločena
• Povezava: https://creativecommons.org/licenses/by/3.0/deed.sl
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Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: trifluorometiltio sulfoksimini, oksidacija, zelena kemija, natrijev hipoklorit pentahidrat

Projekti

• Financer: ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
• Številka projekta: P1-0230
• Naslov: Organska kemija: sinteza, struktura in aplikacija

• Financer: ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
• Program financ.: Young Researchers