1402140-68-4Relevant academic research and scientific papers
Suzuki-Miyaura cross-coupling of 3,4-disubstituted 5-bromoisoxazoles: An efficient access to trisubstituted isoxazoles
Morita, Taiki,Nakamura, Hiroyuki,Tsuda, Masato
, (2021/06/07)
The Suzuki-Miyaura cross-coupling of 3,4-disubstituted 5-bromoisoxazoles 1 at the C5 position has successfully proceeded in the presence of Pd2(dba)3 and P(t-Bu)3·HBF4 catalysts to give the corresponding trisubstituted isoxazoles 3 in good to high yields while suppressing the formation of ketone 4 as a byproduct. The use of bulky phosphine ligand P(t-Bu)3·HBF4 is essential for the current transformation, and the formation of ketone 4, which was a major product in the previous report, was able to be suppressed under the current conditions.
Copper-catalyzed synthesis of trisubstituted isoxazoles via a cascade cyclization-migration process
Ueda, Masafumi,Sugita, Shoichi,Sato, Aoi,Miyoshi, Tetsuya,Miyata, Okiko
, p. 9344 - 9351,8 (2012/12/11)
An atom-economical, catalytic, and regioselective synthesis of 3,4,5-trisubstituted isoxazoles has been successfully developed. Treatment of O-arylmethyl alkynyl oxime ethers with 5 mol % of Cu(OTf)2 in chlorobenzene at reflux gave 4-arylmethylisoxazoles in good to excellent yields via the sequential intramolecular addition of the oxime moiety to the alkyne with subsequent 1,3-migration of the arylmethyl group.
