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Hypervalent Iodine(III)-Mediated Cyclization of Unsaturated N-Alkoxyureas: Cationic Oxybromination vs. Radical Aminobromination and Aminooxyamination

preprint
submitted on 05.07.2019 and posted on 05.07.2019 by Laure Peilleron, Pascal Retailleau, Kevin Cariou
In this study we describe the reactivity of unsaturated N-alkoxyureas in the presence of different combinations of a hypervalent iodine(III) reagent and a bromide source or TEMPO. Three complementary cyclizations can be achieved depending on the reaction conditions. On the one hand, PIFA with pyridinium bromide leads to an oxybromination reaction. On the other hand, bis(tert-butylcarbonyloxy)iodobenzene with tetrabutylammonium bromide or TEMPO triggers aminobromination or aminooxyamination reactions, respectively. Control experiments showed that while the first process is ionic, the other two follow a radical manifold.

History

Email Address of Submitting Author

kevin.cariou@cnrs.fr

Institution

CNRS-ICSN

Country

France

ORCID For Submitting Author

0000-0002-5854-9632

Declaration of Conflict of Interest

No conflict of interest

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