Radical Decyanations of Unactivated Carbon‐CN Bonds: Recent Achievements and Mechanistic Studies

• Published in: Advanced synthesis & catalysis Vol. 365; no. 13; pp. 2058 - 2091
• Main Authors: Huang, Jiapian, Chen, Zhiyuan
• Format: Journal Article
• Language: English
• Published: Heidelberg Wiley Subscription Services, Inc 04.07.2023
• Subjects: Chemical synthesis; Cyano groups; decyanation; electrochemistry; Medical materials; Medical research; nitrile; photo reaction; radical reaction; Transformations
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.202300281

Decyanation is an important process in the synthesis of aromatic molecules in the studies of pharmaceutical research, medical and materials sciences. In late‐stage modifications of privileged carbo/heterocyclic scaffolds, radical‐type decyanation techniques have been devised to date. As a result, the chemistry of cyano‐involved conversions, a hotly debated subject over the past few decades, has advanced significantly. The cyano group (CN), on the other hand, has rarely been acknowledged as a good reaction site due to its thermodynamic robustness. The most recent advancements in catalytic radical decyanation protocols that CN behaved as a leaving group has made are surveyed in this article. Following the introduction of a number of different reaction modes, the catalytic reactions that are used to activate the C−CN bonds are primarily categorized, and the text herein are divided into three groups: (1) photo‐catalyzed decyanation transformations, (2) electro‐catalyzed decyanation transformations, and (3) transition‐metal‐catalyzed or metal‐free decyanation transformations. With an emphasis on the catalytic systems and synthetic applications in C−CN bond activation, this review will provide the readers with an overview of decyanation chemistry in radical reactions.