Related Experiment Video
Updated: Sep 23, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Metal- and Photocatalyst-Free Sulfonylcyanation of [1.1.1]Propellane with Sulfonyl Cyanide
Yuying Wang1, Jianyang Dong1, Dong Xue1
1Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710119, People's Republic of China.
Background:
Bicyclo[1.1.1]pentanes (BCPs), recognized as bioisosteres for paradisubstituted benzene rings, have gained prominence as valuable bioactive scaffolds in drug research.
Methods:
This study describes a radical-coupling method for the synthesis of sulfonyl-, cyanosubstituted BCPs from sulfonyl cyanide and [1.1.1]propellane. In this study, the synthetic schemes were designed to show the chemical reactions. Nuclear Magnetic Resonance (NMR) and Mass Spectrometry (MS) were used to identify and characterize the final compounds.
Results:
This method does not require photocatalysts, metals, or light, generating BCP nitriles as a useful building block. The synthetic potential of this mild protocol was showcased by the diverse transformations.
Conclusion:
This versatile method significantly expands the range of BCP-type bioisosteres that can be generated.
Related Concept Videos
Preparation and Reactions of Sulfides
Preparation of Nitriles
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
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...
![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)