Scandium-Catalyzed Benzylic C(sp3)-H Alkenylation of Tertiary Anilines with Alkynes

This work describes the chemo- and stereoselective benzylic C(sp(3))-H alkenylation of tertiary ortho-methyl anilines with internal alkynes using a simple beta-diketiminato scandium catalyst. This protocol offers an efficient method for the synthesis of a new family of tertiary ortho-allylanilines in high yields. The resultant alkenylation products facilely underwent further chemical transformation to other valuable anilines. A cationic scandium benzyl species was isolated from a stoichiometric reaction and confirmed to be the catalytic intermediate.

Automated summary

This work presents a chemo- and stereoselective benzylic C(sp(3))-H alkenylation of tertiary ortho-methyl anilines with internal alkynes using a beta-diketiminato scandium catalyst. The protocol offers an efficient method for synthesizing a new family of tertiary ortho-allylanilines in high yields, which can be further transformed into other valuable anilines. A cationic scandium benzyl species was identified as the catalytic intermediate.