ABSTRACT
A novel palladium-catalyzed three-component carbonylation reaction for the assembly of various 1,3-substituted maleimide derivatives from haloalkynes and simple anilines. The nucleophilic addition reaction of haloalkynes, anilines and CO, and insertion of carbonyl have been achieved sequentially in this reaction. The high chemo- and regioselectivities, as well as no need of expensive ligands or additives further illustrate the synthetic value of this approach.
ABSTRACT
A novel and efficient palladium-catalyzed annulation of anilines with bromoalkynes for the synthesis of 2-phenylindoles has been described. This approach features excellent regio- and stereoselectivities and good functional group tolerance. Preliminary mechanistic studies indicate that anilines undergo anti-nucleophilic addition to bromoalkynes to generate (Z)-N-(2-bromo-1-phenylvinyl) anilines, followed by sequential C-H functionalization to deliver different substituted 2-phenylindoles. This method provides potential applications for the construction of various biologically active compounds.
ABSTRACT
This report discloses a novel Pd-catalyzed sequential three-component multiple reaction of alkenes, bromoalkynes, and boronic acids using alkenes as hydride and alkenyl donors, leading to highly stereoselective assembly of (Z,E)-1,3-diene derivatives. Mechanistic studies demonstrate that the generation and reutilization of palladium hydride species are critical to the success of this transformation. In addition, the good functional group compatibility, late-stage modification, and investigation of photophysical properties of 1,3-diene products illustrate the synthetic value of this strategy.
