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Catalytic Friedel-crafts reactions on saturated heterocycles and small rings for sp³-sp² coupling of medicinally relevant fragments

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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