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Synthesis 2020; 52(07): 1140-1146
DOI: 10.1055/s-0039-1690795
DOI: 10.1055/s-0039-1690795
paper
Solvent-Free and Liquid-Phase Iodination of Thiophene Derivatives with Potassium Dichloroiodate Monohydrate
Funding from the University of South Dakota Department of Chemistry is appreciated.Further Information
Publication History
Received: 13 October 2019
Accepted after revision: 29 December 2019
Publication Date:
23 January 2020 (online)
† Deceased
Abstract
Iodination of a series of benzene and thiophene derivatives by potassium dichloroiodate monohydrate was studied with and without a solvent. The liquid substrates tend to be more reactive in water while the solid substrates afford better yields in dichloromethane or under the solvent-free conditions. The 2-substituted thiophenes show good to excellent yields whereas the yield for 3-substituted and 3,4- or 2,4-disubstituted thiophenes and benzene derivatives are significantly lower. The mechanochemical reaction of 5-carbaldehyde-2,2′-bithiophene shows excellent yields, while 2,2′-bithiophene gives practical yields only in dichloromethane. In the case of thiophene and N-acetyl-p-toluidine, electrophilic iodination is accompanied by a small extent of chlorination.
Keywords
iodination - thiophene derivatives - mechanochemical reaction - benzene derivatives - inverse-gated NMRSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690795.
- Supporting Information
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