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

This Communication describes the Pd-catalyzed C(sp3)-H functionalization of a tropane derivative to generate products with functionalization at two (beta/gamma) or three (beta/gamma/beta) 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 beta/gamma/beta-functionalized allylic arylation and allylic acetoxylation products.

Automated summary

This study describes the Pd-catalyzed C(sp3)-H functionalization of a tropane derivative, resulting in functionalization at two (beta/gamma) or three (beta/gamma/beta) different positions on the alicyclic amine core. The reaction involves initial dehydrogenation to generate alkene products, which can further react to form a Pd(I) alkene-bridged dimer. Functionalization of this dimer leads to beta/gamma/beta-functionalized allylic arylation and allylic acetoxylation products.