Alkene Difunctionalization Directed by Free Amines: DiamineSynthesis via Nickel-Catalyzed 1,2-Carboamination

A versatile method to access differentially substituted1,3- and 1,4-diamines via nickel-catalyzed three-component 1,2-carboamination of alkenyl amines with aryl/alkenylboronic esternucleophiles and N-O electrophiles is reported. The reaction proceedsefficiently with free primary and secondary amines without needing adirecting auxiliary or protecting group and is enabled byfine-tuning theleaving group on the N-O reagent. The transformation is highlyregioselective and compatible with a wide range of coupling partners and alkenyl amine substrates, all performed at roomtemperature. A series of kinetic studies support a mechanism in which alkene coordination to the nickel catalyst is turnover-limiting.

Automated summary

This study presents a versatile method for accessing differentially substituted 1,3- and 1,4-diamines through nickel-catalyzed three-component 1,2-carboamination of alkenyl amines. The reaction is efficient, regioselective, and compatible with a wide range of coupling partners, all performed at room temperature.