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

Abstract

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.

Suzuki–Miyaura Cross-Coupling Reaction with Potassium Aryltrifluoroborate in Pure Water Using Recyclable Nanoparticle Catalyst

“…1 Potassium aryltrifluoroborate is a very appealing reagent for carbon-carbon bond formation with various electrophiles in the presence of transition metals and has emerged as attractive and promising alternative to arylboronic acid that easily undergo protodeboronation. In addition to Suzuki-Miyaura cross-coupling reaction 2,3 which is the most reported, potassium aryltrifluoroborate is used for the synthesis of N-arylisoindolinone derivatives, 4 3,3-disubstituted heterocycles, 5 aryl ketones, 6 aryl esters, 7 diarylamines, 8 benzofuran derivatives, 6c,9 diaryl alcohol, 10 and so on.…”