Ester dance reaction on the aromatic ring

Kaoru Matsushita, Ryosuke Takise, Kei Muto, Junichiro Yamaguchi*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)


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.

Original languageEnglish
Article numberaba7614
JournalScience Advances
Issue number28
Publication statusPublished - 2020 Jul

ASJC Scopus subject areas

  • General


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