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: dongli
mail.hbut.edu.cn
X. Wang, P. Yang, B. Hu, Q. Zhang, D. Li, J. Org. Chem., 2021, 86, 2820-2826.
DOI: 10.1021/acs.joc.0c02767
Abstract
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
