Diazo compounds and palladium-aryl complexes: trapping the elusive carbene migratory insertion organometallic products

The reactions of Pd-aryl complexes with diazo compounds N2CH-CH=CHPh and N2CHPh allowed us to isolate the organometallic products formed right after the migratory insertion of a non-stabilized CHR carbene into the Pd-aryl bond. eta(3)-Allylic and eta(3)-benzylic palladium complexes were formed respectively. This is compelling experimental evidence for the key step in the palladium-catalyzed cascade transformations of diazo derivatives leading to multiple C-C or C-X bond formation.

Automated summary

The reactions of Pd-aryl complexes with diazo compounds N2CH-CH=CHPh and N2CHPh were studied, and it was found that the migratory insertion of a non-stabilized CHR carbene into the Pd-aryl bond led to the formation of eta(3)-allylic and eta(3)-benzylic palladium complexes. This provides compelling experimental evidence for the key step in the palladium-catalyzed cascade transformations of diazo derivatives.