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Synthesis of trifluoromethylated isoxazoles and their elaboration through inter- and intra-molecular C-H arylation

Browne, Duncan L., Ley, Steven V., Poh, Jian-Siang, Blakemore, David C., Meroni, Francesca, García-Ruiz, Cristina and Zuniga, Andrea 2016. Synthesis of trifluoromethylated isoxazoles and their elaboration through inter- and intra-molecular C-H arylation. Organic & Biomolecular Chemistry 14 (25) , pp. 5983-5991. 10.1039/C6OB00970K

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Abstract

We report conditions for the preparation of a range of trifluoromethylated isoxazole building blocks through the cycloaddition reaction of trifluoromethyl nitrile oxide. It was found that controlling the rate (and therefore concentration) of the formation of the trifluoromethyl nitrile oxide was critical for the preferential formation of the desired isoxazole products versus the furoxan dimer. Different conditions were optimised for both aryl- and alkyl- substituted alkynes. In addition, the reactivity at the isoxazole 4-position has been briefly explored for these building blocks. Conditions for intermolecular C-H arylation, lithiation and electrophile quench, and alkoxylation were all identified with brief substrate scoping that signifies useful tolerance to a range of functionalities. Finally, complementary processes for structural diversification through either intramolecular cyclisation or intermolecular cross-coupling were developed.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Funders: Engineering and Physical Sciences Research Council
Date of First Compliant Deposit: 23 May 2016
Date of Acceptance: 20 May 2016
Last Modified: 21 Jan 2021 13:04
URI: https://orca.cardiff.ac.uk/id/eprint/91157

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