The first example of the palladium-catalyzed sequential nucleophilic addition followed by an intramolecular cyclization of functionalized nitriles with arylboronic acids has been achieved, providing an efficient synthetic pathway to access structurally diverse isoquinolines and isoquinolones. This methodology has also been successfully applied to the total synthesis of the topoisomerase I inhibitor CWJ-a-5 (free base).

A palladium-catalyzed tandem addition/cyclization of 2-(2-aminoaryl)acetonitriles with arylboronic acids has been developed for the first time, achieving a new strategy for direct construction of indole skeletons. This system shows good functional group tolerance and remarkable chemoselectivity. In particular, the halogen (e.g., bromo and iodo) substituents are amenable to further synthetic elaborations thereby broadening the diversity of the products. Preliminary mechanistic experiments indicate that this transformation involves sequential nucleophilic addition followed by an intramolecular cyclization.

Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids for the synthesis of diverse isoquinolines in water.

An efficient rhodium(iii)-catalyzed C–H activation followed by intermolecular annulation between enamides and sulfoxonium ylides has been developed.

A palladium-catalyzed tandem reaction of cyanomethyl benzoates with arylboronic acids has been achieved. Substitution at the 2-position of cyanomethyl benzoates was found to be crucial for the selective synthesis of oxazoles and isocoumarins. Cyanomethyl benzoates afforded 2,4-diaryloxazoles as products, while 2-benzoyl-substituted cyanomethyl benzoates delivered 3-benzoyl-4-aryl-isocoumarins selectively. Furthermore, a possible mechanism for the selective reaction of cyanomethyl benzoates with arylboronic acids was discussed.