C(sp<sup>2</sup>)–H Hydroxylation via Catalytic 1,4-Ni Migration with N<sub>2</sub>O
Huihui Zhang, Jesus Rodrigalvarez, Rubén Martı́n
Abstract
Herein, we report a Ni-catalyzed C(sp 2 )–H hydroxylation of aryl bromides with N 2 O as an oxygen-atom donor. The reaction is enabled by a 1,4-Ni translocation that results in ipso/ortho difunctionalized products. Regioselectivity and stereocontrol are dictated by a judicious choice of the ligand backbone, thus giving access to either carbonyl or phenol derivatives and offering an opportunity to repurpose hazardous substances en route to valuable oxygen-containing building blocks.
Topics & Concepts
ChemistryHydroxylationRegioselectivityCatalysisLigand (biochemistry)ArylMedicinal chemistryPhenolOxygen atomOxygenCombinatorial chemistryOrganic chemistryMoleculeAlkylEnzymeBiochemistryReceptorCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis