Related Experiment Video
Updated: Sep 30, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Rhodium-catalyzed ortho-deuteration of anilines
Annick Vander Eyken1, Gwilherm Evano1,2
1Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB) Avenue F. D. Roosevelt 50, CP160/06 1050 Brussels Belgium gwilherm.evano@ulb.be.
Abstract:
A practical and highly regioselective rhodium-catalyzed protocol for the site-selective ortho-deuteration of anilines via a traceless aminophosphine directing group is reported. The method relies on readily available [Rh(COD)Cl]2 as catalyst and heavy water as an inexpensive and operationally simple deuterium source, and proceeds under mild conditions. Complete regioselectivity for the ortho and ortho' positions is consistently achieved, with high levels of deuterium incorporation as well as broad functional group tolerance. The deuteration moreover extends beyond simple anilines to more complex scaffolds, including tetrahydroisoquinolines, carbazoles, diarylamines or naphthylamines.
More Related Videos
12:27Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
Related Concept Videos
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Diazonium Group Substitution: –OH and –H
α-Alkylation of Ketones via Enolate Ions
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...