Related Experiment Video
Updated: May 31, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Cp*Co(III)-catalyzed ortho-alkylation/alkenylation of anilides
Yongqi Yu1, Jiajia Yu1, Yanqi Li1
1College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, 473061, P. R. China. yuyq2021@163.com.
Abstract:
A highly practical and efficient Cp*Co(III)-catalyzed C-H alkylation/alkenylation reaction of anilides with maleimides and acrylates was developed, during which a weakly coordinating amide carbonyl group functioned as the directing group. This approach features high efficiency, good functional group tolerance, and broad substrate scope, and a variety of 3-substituted succinimides and ortho-alkenylated anilides were synthesized in moderate to excellent yields. Furthermore, the reaction is highly selective, affording mono-ortho-alkylated/alkenylated products only. In addition, synthetic transformations of the 3-substituted succinimide products demonstrate the practicability of the reaction.
More Related Videos
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
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
Related Concept Videos
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
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...
α-Alkylation of Ketones via Enolate Ions
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Preparation of Amines: Alkylation of Ammonia and Amines
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...