Mostafa, M. A.B., Bowley, R. M., Racys, D. T., Henry, M. C. and Sutherland, A. (2017) Iron(III)-catalyzed chlorination of activated arenes. Journal of Organic Chemistry, 82(14), pp. 7529-7537. (doi: 10.1021/acs.joc.7b01225) (PMID:28661157)
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Abstract
A general and regioselective method for the chlorination of activated arenes has been developed. The transformation uses iron(III) triflimide as a powerful Lewis acid for the activation of N-chlorosuccinimide and the subsequent chlorination of a wide range of anisole, aniline, acetanilide and phenol derivatives. The reaction was utilized for the late-stage mono- and di-chlorination of a range of target compounds such as the natural product nitrofungin, the antibacterial agent chloroxylenol and the herbicide chloroxynil. The facile nature of this transformation was demonstrated with the development of one-pot tandem iron-catalyzed dihalogenation processes allowing highly regioselective formation of different carbon-halogen bonds. The synthetic utility of the resulting dihalogenated aryl compounds as building blocks was established with the synthesis of natural products and pharmaceutically relevant targets.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Henry, Mr Martyn and Racys, Dr Daugirdas and Mostafa, Mohamed and Sutherland, Professor Andrew |
| Authors: | Mostafa, M. A.B., Bowley, R. M., Racys, D. T., Henry, M. C., 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: | 29 June 2017 |
| Copyright Holders: | Copyright © 2017 American Chemical Society |
| First Published: | First published in Journal of Organic Chemistry 82(14): 7529-7537 |
| Publisher Policy: | Reproduced in accordance with the copyright policy of the publisher |
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