A Selective C–C Bond Cleavage Strategy Promoted by Visible Light
Rafael D. C. Gallo, M.T. Duarte, Amanda F. da Silva, Celso Y. Okada, Victor M. Deflon, Igor D. Jurberg
Abstract
A new visible-light-promoted reaction between aryldiazoacetates and 1,3-diketones allows good yields and selectivities for C-C bond insertions, leading to the corresponding 1,4-dicarbonyl compounds. This transformation is straightforward and highly practical. It tolerates air and moisture and does not require the use of any metals. Mechanistic investigations support the involvement of a key cyclopropanol intermediate derived from an intramolecular rearrangement.
Topics & Concepts
ChemistryIntramolecular forceBond cleavagePhotochemistryCombinatorial chemistryCleavage (geology)Computational chemistryStereochemistryCatalysisOrganic chemistryGeotechnical engineeringFracture (geology)EngineeringCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions