Radical trifunctionalization of hexenenitrile via remote cyano migration

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.