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Synthesis of phenyliodine(III) bis(3-bromopropionate) for an organocatalyzed Markovnikov-type bromo-aminoxidation of vinylarenes

https://doi.org/10.1016/j.gresc.2023.06.001

Sakkani, Nagaraju; Jha, Dhiraj K.; Sadiq, Nouraan; Sharif, Parisa; Zhao, John C.G. (June 2023, Green Synthesis and Catalysis)

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Organocatalytic synthesis of β-enaminyl radicals as the single-electron donors for phenyliodine(III) dicarboxylates: Direct one-pot alkylation-aminoxidation of styrenes

https://doi.org/10.1039/D2OB01826H

Sakkani, Nagaraju; Jha, Dhiraj Kumar; Sadiq, Nouraan; Zhao, John C.-G. (April 2023, Organic & Biomolecular Chemistry)

A direct one-pot alkylation-aminoxidation of styrene derivatives was achieved by using in-situ-generated alkyl and N-oxyl radicals. The corresponding O-alkylated hydroxylamine derivatives were obtained in moderate to good yields. The reaction features the generation of the alkyl radicals from phenyliodine(III) dicarboxylates via an organocatalytic process, the use of phenyliodine(III) dicarboxylates as the source of the alkyl radicals and the oxidant for the generation of the N-oxyl radicals, and the first generation of the β-enaminyl radicals via a HAT process and their use as the single-electron donors.
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Synthesis of α‐Sulfonyl Ketones through a Salicylic Acid‐Catalyzed Multicomponent Reaction Involving Arylsulfonation and Oxidation

https://doi.org/10.1002/slct.202104138

Sakkani, Nagaraju; Jakkampudi, Satish; Sadiq, Nouraan; Zhao, John_C‐G (December 2021, ChemistrySelect)

Abstract 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 andt‐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.
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