Sharif, S. A.I., Calder, E. D.D., Harkiss, A., Maduro, M. and Sutherland, A. (2016) Synthesis of allylic amide functionalized 2H-chromenes and coumarins using a one-pot overman rearrangement and gold(I)-catalyzed hydroarylation. Journal of Organic Chemistry, 81(20), pp. 9810-9819. (doi: 10.1021/acs.joc.6b01881) (PMID:27680202)
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Abstract
A four-step synthesis of allylic trichloroacetimidates bearing a 2-proparyloxyaryl group has been developed from readily available 2-hydroxybenzaldehydes, and these have been used for the preparation of allylic amide derived 2H-chromenes using an Overman rearrangement and a 6-endo-dig hydroarylation. High yields of the 2H-chromenes were achieved using a stepwise approach involving an Overman rearrangement under thermal conditions followed by a hydroarylation reaction with a gold(I) triflimide catalyst. An alternative method where both reactions were performed as a one-pot process was also developed and instead used a gold(I) chloride catalyst activated by silver(I) hexafluoroantimonate for the cycloisomerization step. The allylic amide derived 2H-chromenes were converted to the corresponding coumarin analogues by a pyridinium dichromate (PDC)-mediated chemoselective allylic oxidation.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Sutherland, Professor Andrew and Calder, Mr Ewen and Sharif, Salaheddin Ahmad and Harkiss, Dr Alexander |
| Authors: | Sharif, S. A.I., Calder, E. D.D., Harkiss, A., Maduro, M., and Sutherland, A. |
| College/School: | College of Medical Veterinary and Life Sciences > School of Biodiversity, One Health & Veterinary Medicine 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: | 28 September 2016 |
| Copyright Holders: | Copyright © 2016 The Authors |
| First Published: | First published in Journal of Organic Chemistry 81(20):9810-9819 |
| Publisher Policy: | Reproduced under a Creative Commons License |
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