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Structurally Divergent Lithium Catalyzed Friedel-Crafts Reactions on Oxetan-3-ols: Synthesis of 3,3-Diaryloxetanes and 2,3-Dihydrobenzofurans

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Title: Structurally Divergent Lithium Catalyzed Friedel-Crafts Reactions on Oxetan-3-ols: Synthesis of 3,3-Diaryloxetanes and 2,3-Dihydrobenzofurans
Authors: Croft, RA
Mousseau, JJ
Choi, C
Bull, JA
Item Type: Journal Article
Abstract: The first examples of 3,3-diaryloxetanes are prepared in a lithium-catalyzed and substrate dependent divergent Friedel–Crafts reaction. para-Selective Friedel–Crafts reactions of phenols using oxetan-3-ols afford 3,3-diaryloxetanes by displacement of the hydroxy group. These constitute new isosteres for benzophenones and diarylmethanes. Conversely, ortho-selective Friedel–Crafts reactions of phenols afford 3-aryl-3-hydroxymethyl-dihydrobenzofurans by tandem alkylation–ring opening; the outcome of the reaction diverging to structurally distinct products dependent on the substrate regioselectivity. Further reactivity of the oxetane products is demonstrated, suitable for incorporation into drug discovery efforts.
Issue Date: 10-Oct-2016
Date of Acceptance: 7-Sep-2016
URI: http://hdl.handle.net/10044/1/39877
DOI: https://dx.doi.org/10.1002/chem.201604031
ISSN: 0947-6539
Publisher: Wiley
Start Page: 16271
End Page: 16276
Journal / Book Title: Chemistry - A European Journal
Volume: 22
Issue: 45
Copyright Statement: © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Sponsor/Funder: Engineering & Physical Science Research Council (EPSRC)
Engineering & Physical Science Research Council (E
The Royal Society
Funder's Grant Number: EP/J001538/1
EP/K503733/1
UF140161
Keywords: carbocations
homogeneous catalysis
lithium
oxetanes
oxygen heterocycles
General Chemistry
03 Chemical Sciences
Publication Status: Published
Appears in Collections:Chemistry
Faculty of Natural Sciences



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