Organic Chemistry

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

Kevin Cariou CNRS-ICSN


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.


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Supplementary material

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Thumbnail image of LNP7c_deposit.txt
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LNP7c deposit
Thumbnail image of LNP7r_deposit.txt
download asset LNP7r_deposit.txt 0.32 MB [opens in a new tab]
LNP7r deposit
Thumbnail image of LNP10f-deposit.txt
download asset LNP10f-deposit.txt 0.78 MB [opens in a new tab]
Thumbnail image of LNP10k-deposit.txt
download asset LNP10k-deposit.txt 0.25 MB [opens in a new tab]