<i>Ipso</i>-Nitration of Boronic Esters Enabled by Ferric Nitrate Nonahydrate (Fe(NO<sub>3</sub>)<sub>3</sub>·9H<sub>2</sub>O) in HFIP
Yuzhu Zheng, Zongyi Liu, Qing Huang, Youwei Xie
Abstract
We describe in this work an operationally facile and generally applicable ipso -nitration of boronic esters by Fe(NO 3 ) 3 ·9H 2 O in hexafluoroisopropanol (HFIP), allowing us fast access to various nitroarenes that are currently difficult to obtain via traditional electrophilic C–H nitrations. In contrast to previous deborylative ipso -nitrations, this new protocol utilized less reactive and more stable organoboron reagents and therefore had significantly improved substrate scope and functional group tolerance, which was exemplified in the late-stage ipso -nitration of various natural products, pharmaceuticals, and biologically active molecules.
Topics & Concepts
NitrationChemistryElectrophileReagentFunctional groupNitrateOrganic chemistryCombinatorial chemistryCatalysisPolymerChemical Synthesis and ReactionsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis