Asymmetric α-Functionalization of 2-Alkyl Azaarenes: Synthesis of Tertiary Fluorides Having Vicinal Stereogenic Centers
Related Experiment Video
Updated: Oct 11, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Arko Das1, Harshit Joshi1, Vinod K Singh1
1Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, Uttar Pradesh 208 016, India.
Abstract:
An enantioselective approach for synthesizing fluorinated azaarenes containing vicinal quaternary-tertiary stereocenters is summarized. The chiral copper(I)-phosphine complex binds with the azaarenes followed by Michael addition to unsaturated acyl imidazoles, resulting in α-functionalized products with an excellent level of enantioselectivities (up to 99%), diastereoselectivities (>20:1), and yields (up to 97%). Furthermore, post-functionalization of the acyl imidazole part has also been demonstrated.
More Related Videos
Related Concept Videos
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

