High-valent palladium-promoted formal Wagner-Meerwein rearrangement

Hongmiao Wu, Bin Yang, Lin Zhu, Ronghua Lu, Guigen Li, Hongjian Lu

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

An oxy-palladation, formal Wagner-Meerwein rearrangement and fluorination cascade has been established for generating fluorinated oxazolidine-2,4-diones and oxazolidin-2-ones. The reaction has a broad substrate scope in which both aryl and alkyl groups can be utilized as efficient migrating groups. Experimental evidence suggests that the reaction is initiated by anti-oxy-palladation of the olefin, followed by oxidative generation of an alkyl PdIV intermediate and a concerted migration-fluorination.

Original languageEnglish
Pages (from-to)5804-5807
Number of pages4
JournalOrganic Letters
Volume18
Issue number22
DOIs
StatePublished - Nov 18 2016

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