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

RSC Advances Pub Date: 2015-08-24 DOI: 10.1039/C5RA14621F

Abstract

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 A3-coupling ([a with combining low line]mine–[a with combining low line]ldehyde–[a with combining low line]lkyne). Interestingly, the synthesized compounds show a pronounced solid state fluorescence property due to their restriction of intramolecular rotation in the condensed phase.

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