Regio- and stereo-selective olefinic C-H functionalization of aryl alkenes in ethanol

We report on N,N-bidentate-chelation-assisted alpha- and beta-olefinic C-H alkenylation of aryl alkenes in ethanol to afford aryl dienes/trienes with excellent regio- and stereo-selectivities. The reaction of 2-alkenyl benzylamine and benzoic acid derived substrates proceeded through six-membered exo-cyclometallation and seven-membered endo-cyclometallation. The aerobic protocols feature wide functionality tolerance, high selectivities and yields, mild conditions and scalable preparation, and the directing group can be easily removed to afford Boc-protected amine by simple reduction.

Automated summary

This study reports on the alpha- and beta-olefinic C-H alkenylation of aryl alkenes in ethanol using N,N-bidentate chelation assistance, yielding aryl dienes/trienes with excellent selectivities. The reaction features mild conditions, wide functionality tolerance, and scalable preparation.