ArticleScience advances2020
Ester dance reaction on the aromatic ring.
Article in Science advances, 2020. 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.
- Alkyl-to-Alkyl Palladium Migration Enables Remote C-C Bond Formation.Journal of the American Chemical Society · 2026Article
- Article
- A Catalyst-Controlled Divergent Rearomatization of BN-Benzvalene.Journal of the American Chemical Society · 2026Article
- Positional Isomerization of 1,2-Azaborine through BN-Benzvalene.Journal of the American Chemical Society · 2026Article
- Nickel-Catalyzed cine-Substitution Toward Carbonyl Dance.Chemistry, an Asian journal · 2026Article
- 1,2-Oxygen Transposition on Arenes Enabled by Palladium/Norbornene Cooperative Catalysis.Journal of the American Chemical Society · 2025Article
- Catalyst-controlled directing group translocation in the site selective C-H functionalization of 3-carboxamide indoles and metallocarbenes.Nature communications · 2025Article
- Cu-PromotedInorganic chemistry · 2024Article
- Radical-triggered translocation of C-C double bond and functional group.Nature chemistry · 2024Article
- A para- to meta-isomerization of phenols.Nature chemistry · 2024Article
- Divergent Transformations of Aromatic Esters: Decarbonylative Coupling, Ester Dance, Aryl Exchange, and Deoxygenative Coupling.Accounts of chemical research · 2024Article
- Article
- A C-to-O atom-swapping reaction sequence enabled by Ni-catalyzed decarbonylation of lactones.Chemical science · 2022Article
Corrections and comments
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Aromatic rearrangement reactions are useful tools in the organic chemist's toolbox when generating uncommon substitution patterns. However, it is difficult to precisely translocate a functional group in (hetero) arene systems, with the exception of halogen atoms in a halogen dance reaction. Here, we describe an unprecedented "ester dance" reaction: a predictable translocation of an ester group from one carbon atom to another on an aromatic ring. Specifically, a phenyl carboxylate substituent can be shifted from one carbon to an adjacent carbon on a (hetero) aromatic ring under palladium catalysis to often give a thermodynamically favored, regioisomeric product with modest to good conversions. The obtained ester moiety can be further converted to various aromatic derivatives through the use of classic and state-of-the-art transformations including amidation, acylations, and decarbonylative couplings.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.