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Synthesis 2018; 50(06): 1359-1367
DOI: 10.1055/s-0036-1589149
DOI: 10.1055/s-0036-1589149
paper
Efficient Direct Halogenation of Unsymmetrical N-Benzyl- and N-Phenylureas with Trihaloisocyanuric Acids
Further Information
Publication History
Received: 02 October 2017
Accepted after revision: 14 November 2017
Publication Date:
13 December 2017 (online)
Abstract
A simple and efficient methodology for the direct halogenation of N-phenylureas was developed using trihaloisocyanuric acids in acetonitrile at room temperature. This protocol proved to be effective for the construction of N-phenylureas with different patterns of substitution. Additionally, less reactive N-benzylureas were halogenated in the presence of a mixture of trifluoroacetic acid and acetonitrile at room temperature.
Key words
ureas - trihaloisocyanuric acids - halogenation - electrophilic aromatic substitution - arenes - chemoselectivity - regioselectivitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589149.
- Supporting Information
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