Copper-catalyzed dearomative 1, 4-carboxylate rearrangement of 2-carbonateindoles. Issue 1 (17th November 2022)

• Record Type: Journal Article
• Authors: Zhu, Yan; Shao, Ying; Tang, Shengbiao; Sun, Jiangtao
• Is Part Of: Organic chemistry frontiers. Volume 10:Issue 1(2023)
• Page Start: 99
• Page End: 103
• Publication Date: 2022-11-17
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo01647h
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A copper-catalyzed dearomative 1, 4-carboxylated rearrangement of 2-carbonateindoles has been realized. Abstract : A novel dearomative 1, 4-rearrangement reaction of 2-carbonateindoles with aryl diazoacetates has been developed in the presence of a copper catalyst, which might proceed through a tandem formation of a zwitterionic intermediate, intramolecular cyclization and ring-opening reaction to give the final rearrangement products containing an all-carbon quaternary center with two newly formed C–C bonds. In this sequence, the disruption of the aromaticity of indole has been realized, associated with 1, 4-carboxylate rearrangements.