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Hypervalent Iodine Reagent-Promoted Hofmann-Type Rearrangement/Carboxylation of Primary Amides

Xia Wang, Peng Yang, Bo Hu, Qian Zhang and Dong Li*

*School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068, China, Email:

X. Wang, P. Yang, B. Hu, Q. Zhang, D. Li, J. Org. Chem., 2021, 86, 2820-2826.

DOI: 10.1021/acs.joc.0c02767


Hypervalent iodine reagents promote a facile and efficient transformation of primary amides to secondary amides. The hypervalent iodine reagent mediates a Hofmann-type rearrangement to an isocyanate intermediate, which is subsequently trapped by an in situ generated carboxylic acid from the hypervalent iodine reagent to provide the corresponding secondary amides.

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proposed mechanism

Key Words

Hofmann Rearrangement, rearrangements, carboxylation, hypervalent iodine compounds

ID: J42-Y2021