Synthesis of 3,3-Disubstituted Heterocycles by Pd-Catalyzed Arylallylation of Unactivated Alkenes

High Resolution Image Download MS PowerPoint Slide Finding new methods of carbon–carbon bond formation is a key goal in expanding current methodology for heterocycle formation. Because of their inherently nonplanar shape, new methods of forming sp 3 -rich scaffolds are of particular importance. Although there are methods for combining heterocyclization and formation of new sp 3 –sp 3 carbon–carbon bonds, these form the carbon–heteroatom bond rather than a carbon–carbon bond of the heterocycle. Here, we show a new alkene arylallylation reaction that generates a heterocycle with concomitant formation of two new carbon–carbon bonds. Furthermore, we demonstrate that this process occurs through an isohypsic (redox neutral) mechanism. Overall, this carboallylation reaction gives a new route to the synthesis of 3,3-disubstituted heterocycles.