A Pd-catalyzed spirocyclization involving a sequential carbopalladation, intramolecular C-H activation, and a highly regioselective alkyne insertion to afford spirooxindoles and spirodihydrobenzofurans has been achieved. The spirocyclic products were generated in good to excellent yields with complete regiocontrol in a readily scalable procedure.

The visible-light-mediated three-component dicarbofunctionalization of styrenes using simple benzylic radicals is described. Notably, this work describes a rare example of undirected dicarbofunctionalization using unsubstituted benzyl radicals. Key to the success of this strategy was the rational design and use of benzylic pyridinium salts as radical precursors. Using this approach, abundant styrenes, electron-rich heterocycles and benzylic amines were combined to rapidly afford a number of densely functionalized 1,1-diarylalkanes. A dipeptide derived pyridinium salt was applied to that transformation, which resembles a visible-light mediated deaminative generation of radicals from peptides.

A novel nickel-catalyzed cycloisomerization reaction forming a new carbon-carbon bond while preserving the carbon-halogen bond has been developed. A cheap and readily available Ni-catalyst is employed to generate nitrogen containing heterocycles in good to excellent yields and the procedure is readily scalable. The more readily available aryl bromides were also cyclized with the addition of potassium iodide to generate the respective alkyl iodides. A rare dual ligand system employing a bisphosphine and bisphosphine monoxide was used to achieve enantioenriched products.

A palladium-catalyzed spirocyclization forming spirooxindoles and spirodihydrobenzofurans has been achieved. Mechanistic studies suggest that the transformation proceeds through sequential carbopalladation, C-H activation, and benzyne insertion. Both classes of spirocycles have been synthesized in good to excellent yields, and the procedure is readily scalable.

The mechanism of the palladium-catalyzed spirocyclization of acrylamides with arynes and alkynes has been computationally and experimentally studied.