Related Experiment Video
Updated: Aug 31, 2025
![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
Visible-light photocatalytic radical addition-translocation-cyclization to construct sulfonyl-containing azacycles
Yu-Qing Liang1, Yi-Xin Xu1, Zhong-Jian Cai1
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, China. zjcai@suda.edu.cn.
Abstract:
Herein, a novel visible-light photocatalytic radical addition-translocation-cyclization (RATC) approach for the efficient synthesis of sulfonyl-containing azacycles is described. The reaction delivers a wide range of monocyclic, bicyclic and polycyclic azacycles by using easily prepared sodium sulfinates and N-homopropargylic amines as starting materials. Instead of the traditionally used toxic tin reagents and thermally hazardous azos in the RATC process, clean, renewable and sustainable visible light combined with a catalytic amount of photosensitizer is used in this process. Moreover, the successful transformation of some drug derivatives further highlights the potential application of this procedure.
Related Concept Videos
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Cycloaddition Reactions: Overview
Radical Formation: Addition
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
![[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)
