Related Experiment Video
Updated: May 2, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Iridium-catalyzed ortho-C-H borylation of aromatic aldimines derived from pentafluoroaniline with
Ikuo Sasaki1, Tatsunosuke Amou, Hajime Ito
1Division of Chemical Process Engineering, Frontier Chemistry Center (FCC), Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan. ishiyama@eng.hokudai.ac.jp.
Abstract:
The development of an Ir-catalyzed ortho-C-H borylation of aromatic aldimines derived from pentafluoroaniline is reported. This reaction proceeded at 120 °C to afford the corresponding borylated products in high yield with good regioselectivity using an Ir complex formed in situ from [Ir(OMe)(cod)]2/2(C6F5)3P in the presence of 2-norbornene.
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Hydroboration-Oxidation of Alkenes
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...

![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)