Palladium-Catalyzed Tandem Diolefination Reaction of Benzaldehyde Enabled by a Remote Directing Group

A tandem diolefination reaction of benzaldehyde has beendevelopedvia Pd-catalyzed & beta;-C(sp(2))-H olefination ofthe benzene ring and tandem C(sp(2))-H olefinationof acrylate. 2-((Aminooxy)methyl)benzonitrile was involved with thebenzaldehyde substrate as a remote directing group to realize theC-H bond activation. The control experiments proved that thepresence of a remote cyano group is essential for this novel diolefinationreaction.

Automated summary

A tandem diolefination reaction of benzaldehyde has been developed via Pd-catalyzed β-C(sp(2))-H olefination of the benzene ring and tandem C(sp(2))-H olefinationof acrylate. Remote directing group 2-((Aminooxy)methyl)benzonitrile was used in conjunction with the benzaldehyde substrate for C-H bond activation. Control experiments demonstrated the essential role of a remote cyano group in this novel diolefination reaction.