Radical Arylation of Triphenyl Phosphite Catalyzed by Salicylic Acid: Mechanistic Investigations and Synthetic Applications
Manel Estruch-Blasco, Diego Felipe‐Blanco, Irene Bosque, José C. González‐Gómez
Abstract
A straightforward and scalable methodology to synthesize diphenyl arylphosphonates at 20 °C within 1-2 h is reported using inexpensive SA as the catalytic promoter of the reaction. Mechanistic investigations suggest that the reaction proceeds via radical-radical coupling, consistent with the so-called persistent radical effect. The reaction tolerated a wide range of functional groups and heteroaromatic moieties. The synthetic usefulness and the unique reactivity of the obtained phosphonates were demonstrated in different one-step transformations.
Topics & Concepts
ChemistryReactivity (psychology)CatalysisSalicylic acidFree-radical reactionCombinatorial chemistryRadicalReaction conditionsFunctional groupCoupling reactionOrganic chemistryBiochemistryMedicineAlternative medicinePathologyPolymerRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods