Direct C-H sulfenylation of quinoxalinones with thiols under visible-light-induced photocatalyst-free conditions

• Published in: Green chemistry : an international journal and green chemistry resource : GC Vol. 21; no. 23; pp. 6241 - 6245
• Main Authors: Teng, Qing-Hu, Yao, Yan, Wei, Wen-Xiu, Tang, Hai-Tao, Li, Jia-Rong, Pan, Ying-Ming
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 2019; Royal Society of Chemistry
• Subjects: Catalysts; Chemistry; Chemistry, Multidisciplinary; Coupling; Dehydrogenation; Green & Sustainable Science & Technology; Green chemistry; Light effects; Oxidants; Oxidizing agents; Photocatalysts; Physical Sciences; Science & Technology; Science & Technology - Other Topics; Thiols; POTENT; DESIGN; ANTICANCER; ARYLATION; AGENTS; QUINOXALIN-2(1H)-ONES; INHIBITORS; FACILE; ACCESS; TRIFLUOROMETHYLATION
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/c9gc03045j

A photocatalyst-free visible-light-promoted sulfenylation of quinoxalinones with thiols via cross-dehydrogenative coupling was developed. This protocol allowed the direct formation of diverse 3-sulfenylquinoxalin-2(1 H )-ones under metal- and catalyst-free conditions and using air (O 2 ) as an oxidant. Furthermore, a range of readily accessible thiols and quinoxalin-2(1 H )-ones was applied in this coupling, resulting in an attractive process of accessing 3-substituted quinoxalinones. We have developed a metal-free and catalyst-free visible-light-promoted direct C-H sulfenylation of quinoxalin-2(1 H )-ones with thiols for the synthesis of diverse 3-sulfenylquinoxalin-2(1 H )-ones.