Visible-Light-Mediated Strategies for the Preparation of Oxime Ethers Derived from O–H Insertions of Oximes into Aryldiazoacetates
Mateus L. Stivanin, M.T. Duarte, Luiz Paulo Melchior de Oliveira Leão, Felipe A. Saito, Igor D. Jurberg
Abstract
Two visible-light-mediated O-H insertion protocols involving oximes and aryldiazoacetates leading to different products depending on the solvent employed are reported. In DCM, direct O-H insertion takes place. In THF, there is the additional incorporation of the ring-opened form of this solvent into the structure of the product. These metal-free protocols are mild and tolerant to air and moisture. The preparation of an acaricide has been developed as an example of synthetic application.
Topics & Concepts
ChemistryOximeSolventRing (chemistry)AcaricideBicyclic moleculeCombinatorial chemistryAcetalOrganic chemistryStereochemistryPolymer chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions