Synthesis of trifluoromethylated isoxazoles and their elaboration through inter- and intra-molecular C-H arylation.
Published version
Peer-reviewed
Repository URI
Repository DOI
Type
Change log
Authors
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.
Description
Keywords
Journal Title
Conference Name
Journal ISSN
1477-0539
Volume Title
Publisher
Publisher DOI
Sponsorship
Engineering and Physical Sciences Research Council (EP/M004120/1)