Waddell, L. J.N., Senkans, M. R. and Sutherland, A. (2023) Regioselective C–H thiocyanation of arenes by iron(III) chloride catalysis. Journal of Organic Chemistry, 88(11), pp. 7208-7218. (doi: 10.1021/acs.joc.3c00454) (PMID:37158540)
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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.
| Item Type: | Articles |
|---|---|
| Additional Information: | Financial support from EPSRC (studentship to L.J.N.W., EP/T517896/1) and the University of Glasgow is gratefully acknowledged. |
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Sutherland, Professor Andrew and Waddell, Mr Lachlan |
| Authors: | Waddell, L. J.N., Senkans, M. R., and Sutherland, A. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Journal of Organic Chemistry |
| Publisher: | American Chemical Society |
| ISSN: | 0022-3263 |
| ISSN (Online): | 1520-6904 |
| Published Online: | 09 May 2023 |
| Copyright Holders: | Copyright © 2023 The Authors |
| First Published: | First published in Journal of Organic Chemistry 88(11): 7208-7218 |
| Publisher Policy: | Reproduced under a Creative Commons License |
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