High-Valent Palladium-Promoted Formal Wagner-Meerwein Rearrangement

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

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Abstract

An oxy-palladation, formal Wagner-Meerwein rearrangement and fluorination cascade has been established for generating fluorinated oxazolicline-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 antioxy-palladation of the olefin, followed by oxidative generation of an alkyl Pd-IV intermediate and a concerted migration fluorination.
Original languageEnglish
Pages (from-to)5804-5807
JournalOrganic Letters
StatePublished - Nov 2016

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Wu, H., Yang, B., Zhu, L., Lu, R., Li, G., & Lu, H. (2016). High-Valent Palladium-Promoted Formal Wagner-Meerwein Rearrangement. Organic Letters, 5804-5807.