Ipso-Nitration of Boronic Esters Enabled by Ferric Nitrate Nonahydrate (Fe(NO3)3·9H2O) in HFIP
Related Experiment Video
Updated: Apr 6, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Yuzhu Zheng1, Zongyi Liu1, Qing Huang1
1Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Materials Chemistry and Service Failure, and School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, China.
Abstract:
We describe in this work an operationally facile and generally applicable ipso-nitration of boronic esters by Fe(NO3)3·9H2O 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.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Related Concept Videos
Hydroboration-Oxidation of Alkenes
Alcohols from Carbonyl Compounds: Reduction
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
Electrophilic Aromatic Substitution: Nitration of Benzene
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism