Cobalt-catalyzed C(sp2)-H bond imination of phenylalanine derivatives

Herein we report the cobalt-catalyzed, picolinamide-directed C-H bond imination protocol of phenylalanine derivatives using isocyanides and a Co(dpm)(2) catalyst. A wide range of functional groups were tolerated under the reaction conditions, yielding imines in high yields. The obtained imine products can easily be transformed to 1-aminoisoquinoline derivatives under reductive conditions, providing an attractive alternative to already existing methodologies. The control experiments indicated that C-H activation might occur via an electrophilic pathway.

Automated summary

In this study, we reported a cobalt-catalyzed C-H arylation method using picolinamide as a directing group for phenylalanine derivatives. The reaction displayed good tolerance towards various functional groups and exhibited high yields. The obtained imine products can be easily transformed to 1-aminoisoquinoline derivatives under reductive conditions, providing an attractive alternative. Control experiments suggested that C-H activation might proceed via an electrophilic pathway.