Related Experiment Video
Updated: Mar 8, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Cobalt-Catalyzed Annulation of Amides with Isocyanides via C(sp2)-H Activation
Zheng-Yang Gu1, Cheng-Guo Liu1, Shun-Yi Wang1
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University , Suzhou 215123, P. R. China.
Abstract:
A cobalt-catalyzed [4 + 1] cycloaddition of easily accessible amides with isocyanides for the efficient synthesis of 3-iminoisoindolinone derivatives in high yield under mild conditions via intramolecular C(sp2)-H activation and isocyanide insertion is reported. The annulation was found to be applicable to a broad range of substrates, including arylamides, heteroarylamides, and acrylamide derivatives. Strongly coordinating N-heterocyclic directing groups such as pyridine, pyrimidine, and even pyrazole were fully tolerated in this cobalt-catalyzed C-H activation reaction.
Related Concept Videos
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Nucleophilic Aromatic Substitution: Elimination–Addition
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Cycloaddition Reactions: Overview
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...

![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)