Henry

A procedure for the synthesis of biaryl ketones by a palladium-catalyzed Suzuki–Miyaura cross-coupling reaction between phenyltrifluoroborates and benzoyl chlorides is described. Organotrifluoroborates are unique to other cross-coupling reagents as they have a high functional-group tolerance and are moisture-stable. Moderate to excellent yields were obtained for all substrates tested.

A procedure for the synthesis of biaryl ketones by a Pd-catalyzed Suzuki–Miyaura cross-coupling reaction between phenyltrifluoroborates and benzoyl chlorides with moderate to excellent yields is described. Organotrifluoroborates are unique to other cross-coupling reagents as they have a high functional-group tolerance and are moisture-stable.

The rhodium(III)-catalyzed tandem C–H olefination and cyclization of benzamides with various alkenes is described. This protocol provides direct access to highly substituted phthalides, which are known as crucial frameworks of biologically active compounds. In particular, the amide directing group containing a benzimidazole group facilitates the activation of aromatic ortho-C–H bonds leading to olefination intermediates, and is spantaneously converted into an acid moiety, which can further undergo the intramolecular annulation process.

The site-selective rhodium(III)-catalyzed C–H olefination and cyclization of benzamides with various alkenes by C–H bond activation is described. These transformations allow the generation of an array of C3-substituted phthalides known to be crucial scaffolds of biologically active compounds.

A readily available cyclic carbamate 1 functions as a general precursor to a range of functionalized piperidine products via a new Pd-catalyzed annulation strategy. An asymmetric catalytic variant provides a rapid and efficient means to access these heterocycles with high to excellent levels of enantiocontrol. Finally, these richly functionalized compounds are amenable to further chemoselective elaboration.

To cut a long story short… A cyclic carbamate functions as a general precursor to a range of functionalized piperidine products through a new Pd-catalyzed annulation strategy. An asymmetric catalytic variant provides a rapid and efficient means to access these heterocycles with high to excellent levels of enantiocontrol.