ArticleNature chemistry2021
A ring expansion strategy towards diverse azaheterocycles.
Article in Nature chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed, 104 citations in OpenAlex.
- Conversion of trifluoromethyls into esters along with polyether upcyclingChemical science · 2026Article
- Modular esterification of unstrained carbonyls through palladium-catalyzed alkyne bridging C-C bond activation.Nature communications · 2025Article
- Catalytic asymmetric intermolecular [4 + 2] annulation of benzocyclobutenones with Alkynes and activated carbonyls via C-C activation.Nature communications · 2025Article
- Ring Expansion via Palladium-Catalyzed Aryne Insertion into C-C Bonds of Benzocyclobutenones.Angewandte Chemie (International ed. in English) · 2025Article
- Aza-[4 + 2]-cycloaddition of benzocyclobutenones into isoquinolinone derivatives enabled by photoinduced regio-specific C-C bond cleavage.Nature communications · 2024Article
- Ring Transformation of Cyclopropenes to Benzo-Fused Five-Membered Oxa- and Aza-Heterocycles via a Formal [4+1] Cyclization.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Skeletal Editing: Ring Insertion for Direct Access to Heterocycles.Molecules (Basel, Switzerland) · 2024Review
- Organic Dye-Sensitized Nitrene Generation: Intermolecular Aziridination of Unactivated Alkenes.The Journal of organic chemistry · 2024Article
- Evolution of organic phosphor through precision regulation of nonradiative decay.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
- A Direct Method for Synthesis of Quinoxalines and Quinazolinones Using Epoxides as Alkyl Precursor.Molecules (Basel, Switzerland) · 2023Article
- Construction of azaheterocycles via Pd-catalyzed migratory cycloannulation reaction of unactivated alkenes.Nature communications · 2022Article
- Palladium-Catalyzed Access to Benzocyclobutenone-Derived Ketonitrones via C(spOrganic letters · 2022Article
- Dihydroquinazolinones as adaptative C(spNature communications · 2022Article
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The development of innovative strategies for the synthesis of N-heterocyclic compounds is an important topic in organic synthesis. Ring expansion methods to form large N-heterocycles often involve the cycloaddition of strained aza rings with π bonds. However, in some cases such strategies suffer from some limitations owing to the difficulties in controlling the regioselectivity and the accessibility of specific π-bond synthons. Here, we report the development of a general ring expansion strategy that involves a formal cross-dimerization between three-membered aza heterocycles and three- and four-membered-ring ketones through synergistic bimetallic catalysis. These formal cross-dimerizations of two different strained rings are efficient and scalable, and provide a straightforward and broadly applicable means of assembling diverse N-heterocycles, such as 3-benzazepinones, dihydropyridinones and uracils, which are versatile units in numerous drugs and biologically active compounds. Preliminary mechanistic studies revealed that the C-C bond of strained ring ketones is first cleaved by the Pd
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