Related Experiment Video
Updated: Sep 13, 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
Introducing Azaindole Thianthrenium Salt: An Electrophilic Coupling Partner for Cross-Coupling Reaction
Siddhartha Paul1, Vishal Talukdar1, Parthasarathi Das1
1Department of Chemistry and Chemical Biology, Indian Institute of Technology, Indian School of Mines, Dhanbad826004, India.
Abstract:
Herein, we report a new approach for the C3-H functionalization of azaindoles through thianthrenium salt formation. This versatile azaindole thianthrenium salt intermediate participates in a range of cross-coupling reactions, including Suzuki, Heck, Sonogashira, Hiyama, and Barluenga-Valdés-type coupling. By combining the site-selectivity of thianthrenation with the robustness of these electrophilic reagents, this protocol grants access to a large variety of azaindole derivatives that are otherwise challenging to prepare with comparable levels of selectivity, diversity, and practicality.
More Related Videos
10:42Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
11:45Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Related Concept Videos
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
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...
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...
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene