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Updated: Oct 9, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Radical trifunctionalization of hexenenitrile via remote cyano migration
Chenyang Chang1, Huihui Zhang1, Xinxin Wu1
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China. chzhu@suda.edu.cn.
Abstract:
A novel radical-mediated trifunctionalization of hexenenitriles via the strategy of remote functional group migration is disclosed. A portfolio of functionalized hexenenitriles are employed as substrates. After difunctionalization of the unactivated alkenyl part via remote cyano migration, the in situ formed radical intermediate is captured by an azido radical, thus enabling the trifunctionalization. The reaction features mild conditions and broad functional group compatibility, leading to valuable products bearing multiple useful groups. This protocol further extends the scope of remote functional group migration.
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