Benzimidazolinone synthesis through hypervalent iodine-mediated cycloaddition between aryl isocyanates and O-substituted hydroxylamines

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Authors: Hirotaka Sasa, Haruki Shimada, Kyohei Kitamura, Keita Mizushima, Soshi Yamamoto, Shotaro Hamatani, Toshifumi Dohi
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Abstract

We developed a one-pot cycloaddition methodology for the synthesis of benzimidazolinones, which involves the formation of arylureas using O-benzyl hydroxylamine as a specific nitrogen source, followed by oxidative aromatic C-H amination promoted by hypervalent iodine reagent and catalyst.Our protocol utilized readily available starting materials, thereby enabling rapid access to the target benzimidazolinones.Additionally, the product from this one-pot process was further derivatized to produce an N,N'-disubstituted benzimidazolinone.

Fields of Study & Subjects

Oxidative Organic Chemistry Reactions Synthesis and Reactions of Organic Compounds Organic Chemistry Synthesis Methods

Publication details

Journal / source
ARKIVOC
Volume
2025
Issue
4
Publication date
16 February 2026
Language
EN