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Regioselective C-H Thiocyanation of Arenes by Iron(III) Chloride Catalysis.

ABSTRACT: Aryl thiocyanates are flexible synthetic intermediates that can be used in the preparation of a diverse range of arene building blocks for medicinal chemistry. Here, we report a fast and efficient Lewis acid-catalyzed method for the regioselective thiocyanation of arenes. Iron(III) chloride was found to be an effective Lewis acid for the activation of N-thiocyanatosaccharin and the subsequent thiocyanation of a wide range of activated arenes. The procedure was applicable for the thiocyanation of biologically active compounds such as metaxalone and an estradiol derivative and was used as part of a one-pot tandem iron-catalytic process for the regioselective, dual functionalization of an arene building block.

SUBMITTER: Waddell LJN

PROVIDER: S-EPMC10242756 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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Regioselective C-H Thiocyanation of Arenes by Iron(III) Chloride Catalysis.

Waddell Lachlan J N LJN Senkans Maisie R MR Sutherland Andrew A

The Journal of organic chemistry 20230509 11

Aryl thiocyanates are flexible synthetic intermediates that can be used in the preparation of a diverse range of arene building blocks for medicinal chemistry. Here, we report a fast and efficient Lewis acid-catalyzed method for the regioselective thiocyanation of arenes. Iron(III) chloride was found to be an effective Lewis acid for the activation of <i>N</i>-thiocyanatosaccharin and the subsequent thiocyanation of a wide range of activated arenes. The procedure was applicable for the thiocyana ...[more]

PMID: 37158540

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