ArticleACS catalysis2016
Efficient Benzimidazolidinone Synthesis via Rhodium-Catalyzed Double-Decarbonylative C-C Activation/Cycloaddition between Isatins and Isocyanates.
Article in ACS catalysis, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Skeletal Rearrangements of Amides via Breaking Inert Bonds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Merging the Norrish type I reaction and transition metal catalysis: photo- and Rh-promoted borylation of C-C σ-bonds of aryl ketones.Chemical science · 2023Article
- A directing group switch in copper-catalyzed electrophilic C-H amination/migratory annulation cascade: divergent access to benzimidazolone/benzimidazole.Chemical science · 2022Article
- Nickel-catalyzed skeletal transformation of tropone derivativesChemical science · 2022Article
- Orthogonal cross-coupling through intermolecular metathesis of unstrained C(aryl)-C(aryl) single bonds.Nature chemistry · 2021Article
- Cobalt-Catalyzed Intramolecular Alkyne/Benzocyclobutenone Coupling: C-C Bond Cleavage via a Tetrahedral Dicobalt Intermediate.ACS catalysis · 2018Article
- Distal-Bond-Selective C-C Activation of Ring-Fused Cyclopentanones: An Efficient Access to Spiroindanones.Angewandte Chemie (International ed. in English) · 2017Article
- "Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation.ACS catalysis · 2017Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
The first decarbonylative cycloaddition of less-strained cyclic ketones (isatins) with isocyanates is reported. Initiated by C-C activation, this distinct [5-2+2] transformation provides a rapid entry to access various benzimidazolidinone derivatives, through which a wide range of isocyanates can be efficiently coupled with broad functional group tolerance. A modified one-pot process, combining Curtius rearrangement and C-C activation, was also achieved by using acyl azides as the starting materials. Detailed mechanistic study revealed a surprising double-decarbonylative reaction pathway. The novel reactivity discovered in this basic research is expected to shed light on developing new heterocycle formation methods through a C-C/isocyanate coupling.
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