Transannular Functionalization of Multiple C(sp3)-H Bonds of Tropane via an Alkene-Bridged Palladium(I) Dimer

This Communication describes the Pd-catalyzed C(sp(3))-H functionalization of a tropane derivative to generate products with functionalization at two (ss/gamma) or three (ss/gamma/ss) different sites on the alicyclic amine core. These reactions proceed via an initial dehydrogenation to generate an alkene product that can react further to form a Pd(I) alkene-bridged dimer. Functionalization of this dimer affords ss/./ss-functionalized allylic arylation and allylic acetoxylation products

Automated summary

This study describes the Pd-catalyzed C(sp(3))-H functionalization of a tropane derivative, resulting in products with functionalization at two or three different sites on the alicyclic amine core. The reaction involves dehydrogenation to generate an alkene product, which can further react to form a Pd(I) alkene-bridged dimer. Functionalization of this dimer produces ss/./ss-functionalized allylic arylation and allylic acetoxylation products.