The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound
Yao Liu, Raimon Puig de la Bellacasa, Bo Li, Ana B. Cuenca, Shih‐Yuan Liu
Abstract
The first α-boryl diazo compound that is capable of engaging in classic synthetic organic diazo reaction chemistry is described. The diazomethyl-1,2-azaborine 1, which is a BN isostere of phenyldiazomethane, is significantly more stable than phenyldiazomethane; its reaction chemistry ranges from C–H activation, O–H activation, [3+2] cycloaddition, and halogenation, to Ru-catalyzed carbonyl olefination. The demonstrated broad range of reactivity of diazomethyl-1,2-azaborine 1 makes it an exceptionally versatile synthetic building block for the 1,2-azaborine heterocyclic motif.
Topics & Concepts
ChemistryDiazoCycloadditionHalogenationReactivity (psychology)Medicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryCatalysisAlternative medicinePathologyMedicineCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry Methods