Issue 8, 2021

Iodonium salts as efficient iodine(iii)-based noncovalent organocatalysts for Knorr-type reactions

Abstract

Hypervalent iodine(III)-derivatives display higher catalytic activity than other aliphatic and aromatic iodine(I)– or bromine(I)-containing substrates for a Knorr-type reaction of N-acetyl hydrazides with acetyl acetone to give N-acyl pyrazoles. The highest activity was observed for dibenziodolium triflate, for which 10 mol% resulted in the generation of N-acyl pyrazole from acyl hydrazide and acetyl acetone typically at 50 °C for 3.5–6 h with up to 99% isolated yields. 1H NMR titration data and DFT calculations indicate that the catalytic activity of the iodine(III) is caused by the binding with a ketone.

Graphical abstract: Iodonium salts as efficient iodine(iii)-based noncovalent organocatalysts for Knorr-type reactions

Supplementary files

Article information

Article type
Paper
Submitted
12 nov 2020
Accepted
05 jan 2021
First published
22 jan 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 4574-4583

Iodonium salts as efficient iodine(III)-based noncovalent organocatalysts for Knorr-type reactions

S. N. Yunusova, A. S. Novikov, N. S. Soldatova, M. A. Vovk and D. S. Bolotin, RSC Adv., 2021, 11, 4574 DOI: 10.1039/D0RA09640G

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