Synthesis of α‐Sulfonyl Ketones through a Salicylic Acid‐Catalyzed Multicomponent Reaction Involving Arylsulfonation and Oxidation

• Published in: ChemistrySelect (Weinheim) 2021-12, Vol.6 (47), p.13577-13581
• Main Authors: Sakkani, Nagaraju, Jakkampudi, Satish, Sadiq, Nouraan, Zhao, John C.‐G.
• Format: Article
• Language: English
• Subjects: multicomponent reaction; organocatalysis; radical reaction; salicylic acid; α-sulfonyl ketone
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.202104138

The direct synthesis of α‐sulfonyl ketones was accomplished by a multicomponent reaction of styrene derivatives, anilines, t‐butyl nitrite, 1,4‐diazabicyclo[2.2.2]octane‐sulfur dioxide (DABSO), and oxygen catalyzed by salicylic acid. The aryl radicals generated from aniline derivatives and t‐butyl nitrite under the catalysis of salicylic acid was sulfonylated by DABSO to generate the arylsulfonyl radicals, which reacted further with styrenes, and then oxidized by oxygen to give the title compounds. Under the optimized conditions, the title compounds were obtained in good yields at ambient temperature within 1.5–2 h. This article presents an organocatalyzed multicomponent reaction between styrene derivatives, anilines, t‐butyl nitrite, DABSO, and oxygen at ambient temperature using salicylic acid as the catalyst. The aryl radicals generated from the reaction of aniline derivatives and t‐butyl nitrite under the catalysis of salicylic acid are sulfonylated by DABSO, and the resulting arylsulfonyl radicals react further with styrenes and oxygen to give the corresponding α‐sulfonyl ketones in good yields within 1.5 to 2 h.