Synthesis of tetra-substituted olefins via annulation by Pd-catalyzed carbopalladation/C-H activation and solid state fluorescence properties

Palladium-catalyzed and norbornene-mediated multiple C-C bond forming strategies to highly substituted helical olefin incorporated 1,2,3,4-tetrahydroisoquinolines have been developed via double carbopalladation/C-H activation of 2-bromo-N-benzylpropargylamines. The scope of the above carbocyclization process has been studied by varying the substitution on starting materials which have been synthesized using A(3)-coupling (amine-aldehyde-alkyne). Interestingly, the synthesized compounds show a pronounced solid state fluorescence property due to their restriction of intramolecular rotation in the condensed phase.