High-Valent Palladium-Promoted Formal Wagner-Meerwein Rearrangement.


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 Pd(IV) intermediate and a concerted migration-fluorination.

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@article{Wu2016HighValentPF, title={High-Valent Palladium-Promoted Formal Wagner-Meerwein Rearrangement.}, author={Hongmiao Wu and Bin Yang and Lin Zhu and Ronghua Lu and Guigen Li and Hongjian Lu}, journal={Organic letters}, year={2016}, volume={18 22}, pages={5804-5807} }