Petr Šimůnek

Here, six novel bicyclic and tricyclic difluoroboron NBN and OBN heterocycles were designed for their strong potential as active layers in optoelectronics and responsive units in sensing applications.

A number of β‐enaminones with secondary amino group (alkyl, cyclopropyl, and aryl) were prepared from corresponding β‐diketones. Two general protocols for their palladium‐catalyzed intramolecular C–N cross‐coupling were established to give corresponding N‐substituted condensed tetrahydropyridines in good yields. The methodology is applicable for a wide variety of structural motifs. The work also extends the applicability of novel, recently established, palladium precatalysts to new substrates.

2-Aroylmethylidene-1,2,3,4-tetrahydroquinolines with the appropriate substituents can be suitable precursors for the synthesis of alkaloids from Galipea officinalis (cuspareine, galipeine, galipinine, angustureine). However, only two, rather low-yielding procedures for their synthesis are described in the literature. We have developed a simple and efficient protocol for an intramolecular, palladium or copper-catalysed amination of both chloro- and bromo-substituted 3-amino-1,5-diphenylpent-2-en-1-ones leading to the above-mentioned tetrahydroquinoline moiety. The methodology is superior to the methods published to date.