Ester dance reaction on the aromatic ring

Kaoru Matsushita, Ryosuke Takise, Kei Muto, Junichiro Yamaguchi

Research output: Contribution to journalArticle

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.

Original languageEnglish
Article numberaba7614
JournalScience Advances
Volume6
Issue number28
DOIs
Publication statusPublished - 2020 Jul

ASJC Scopus subject areas

  • General

Fingerprint Dive into the research topics of 'Ester dance reaction on the aromatic ring'. Together they form a unique fingerprint.

Cite this