Related Experiment Video
Updated: Jun 13, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Deoxytrifluoromethylation/aromatization of cyclohexan(en)ones to access highly substituted trifluoromethyl arenes
Pankaj Bhattarai1, Mohammed K Abd El-Gaber1,2, Suvajit Koley1,3
1Borch Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, IN, 47907, USA.
Abstract:
Trifluoromethyl arenes (Ar-CF3) are amongst the commonly encountered fluorinated substructures in pharmaceutical, agrochemical, and material sciences. However, predominant methods to access Ar-CF3 possess several limitations, including harsh conditions, lack of availability of substrates, and poor regioselectivity, which combined restrict access to desirable highly functionalized Ar-CF3-containing compounds. To expand the scope of accessible Ar-CF3-based molecules, we present an orthogonal deoxyfluoroalkylation/aromatization approach that exploits readily accessible and programable cyclohexan(en)one substrates, which undergo a reliable 1,2-addition reaction with the Ruppert-Prakash reagent (TMSCF3) followed by aromatization to deliver highly functionalized Ar-CF3 compounds in a one/two-pot sequence. This general strategy enables access to highly substituted Ar-CF3-containing molecules that are difficult, expensive, and/or impossible to access by current synthetic methods.
More Related Videos
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
07:56Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
Published on: August 12, 2019
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Frost Circles for Different Conjugated Systems
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Carboxylic Acids to Methylesters: Alkylation using Diazomethane