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Structurally Divergent Lithium Catalyzed Friedel-Crafts Reactions on Oxetan-3-ols: Synthesis of 3,3-Diaryloxetanes and 2,3-Dihydrobenzofurans.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2016 Nov 02; Vol. 22 (45), pp. 16271-16276. Date of Electronic Publication: 2016 Oct 10. - Publication Year :
- 2016
-
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 reactions; 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.<br /> (© 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.)
Details
- Language :
- English
- ISSN :
- 1521-3765
- Volume :
- 22
- Issue :
- 45
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 27723135
- Full Text :
- https://doi.org/10.1002/chem.201604031