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Catalytic Friedel-crafts reactions on saturated heterocycles and small rings for sp³-sp² coupling of medicinally relevant fragments
File | Description | Size | Format | |
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MS Heterocycles Friedel-Crafts Final.pdf | Accepted version | 1.25 MB | Adobe PDF | View/Open |
Title: | Catalytic Friedel-crafts reactions on saturated heterocycles and small rings for sp³-sp² coupling of medicinally relevant fragments |
Authors: | Croft, RA Dubois, M Boddy, A Denis, C Lazaridou, A Voisin, AS Bureau, R Choi, C Mousseau, J Bull, J |
Item Type: | Journal Article |
Abstract: | gem-Diarylheterocycles display a wide range of biological activity. Here we present a systematic study into the formation of 4- to 6-membered O- and N-heterocycles and cyclobutanes bearing the diaryl motif through a catalytic Friedel–Crafts reaction from the corresponding benzylic alcohols. 3,3-Diaryltetrahydrofurans, 4,4 diaryltetrahydropyrans, 3,3-diarylpyrrolidines, 4,4-diaryl-piperidines, as well as diarylcyclobutanes are examined, with results for 3,3-diaryloxetanes and 3,3-diarylazetidines presented for comparison. Three catalytic systems are investigated for each substrate [Ca(II), Li(I) and Fe(III)], across preinstalled aromatic groups of differing electronic character. In most cases examined, the diaryl product is obtained directly from the alcohol with good yields using the most appropriate catalyst system. In the absence of a nucleophile, the olefins from the 5- and 6-membered substrates by elimination of water are obtained under the same reaction conditions. |
Issue Date: | 1-Sep-2019 |
Date of Acceptance: | 13-May-2019 |
URI: | http://hdl.handle.net/10044/1/70546 |
DOI: | 10.1002/ejoc.201900498 |
ISSN: | 1099-0690 |
Publisher: | Wiley |
Start Page: | 5385 |
End Page: | 5395 |
Journal / Book Title: | European Journal of Organic Chemistry |
Volume: | 2019 |
Issue: | 31-32 |
Copyright Statement: | © 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer reviewed version of the following article Croft, R.A., Dubois, M.A.J., Boddy, A.J., Denis, C., Lazaridou, A., Voisin‐Chiret, A.S., Bureau, R., Choi, C., Mousseau, J.J. and Bull, J.A. (2019), Catalytic Friedel‐Crafts Reactions on Saturated Heterocycles and Small Rings for sp3‐sp2 Coupling of Medicinally Relevant Fragments. Eur. J. Org. Chem., 2019: 5385-5395, which has been published in final form at https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201900498. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. |
Sponsor/Funder: | Engineering & Physical Science Research Council (EPSRC) The Royal Society The Royal Society The Royal Society |
Funder's Grant Number: | EP/J001538/1 UF140161 RG150444 RGF\EA\180031 |
Keywords: | Science & Technology Physical Sciences Chemistry, Organic Chemistry Oxygen heterocycles Nitrogen heterocycles Small rings Lewis acids Homogeneous catalysis PROTEIN-KINASE-B INTRAMOLECULAR HYDROAMINATION NITROGEN-HETEROCYCLES HIGH-AFFINITY DISCOVERY ALKYLATION ALCOHOLS CONSTRUCTION COMPLEXATION SUBSTITUTION Organic Chemistry 0305 Organic Chemistry 0304 Medicinal and Biomolecular Chemistry |
Publication Status: | Published |
Online Publication Date: | 2019-06-12 |
Appears in Collections: | Chemistry Faculty of Natural Sciences |