title: Synthesis of 3,4,5-trisubstituted isoxazoles via sequential [3 + 2] cycloaddition/silicon-based cross-coupling reactions.
abstract: [reaction: see text] A [3 + 2] cycloaddition reaction between alkynyldimethylsilyl ethers and aryl and alkyl nitrile oxides to produce isoxazolylsilanols has been developed. The cross-coupling reactions of these heterocyclic silanols with a variety of aryl iodides affords 3,4,5-trisubstituted isoxazoles. This sequential process allows for rapid variation of substituents at the 3, 4, and 5 positions of the isoxazole.
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
authors.forename: Scott E
authors.initials: SE
authors.lastname: Denmark
authors.forename: Jeffrey M
authors.initials: JM
authors.lastname: Kallemeyn
mesh_terms: D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D012825:Silicon / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
chemical_list: D007555:Isoxazoles; D012825:Silicon