A preparation of 2-hydroxyamino-2′-iodobiaryls via the Cu-catalyzed enantioselective ring-opening reaction of cyclic diaryliodonium salts with O-alkylhydroxylamines is reported. 3,5-Di(tert-butyl)phenyl bis(oxazoline) was found to be the optimal ligand, and up to 99% ee values were achieved. The use of CaO as the base dramatically improved the yields and inhibited the side reactions. Finally, synthetic applications of these hydroxylamines were briefly demonstrated.

The palladium-catalyzed asymmetric synthesis of enone-based atropisomers from 2-iodo-3-methylcyclohex-2-enones and aryl boronic acid is reported. BoPhoz-type phosphine-aminophosphine ligands showed superior enantioselectivity over other ligands. These cyclohexenone-based atropisomers are useful compounds for further elaboration. The divergent synthesis of biaryl atropisomers with different ortho substituents was demonstrated.

A visible light accelerated C-H functionalization reaction in palladium-catalyzed arylation of vinyl arenes with diaryliodonium salts is reported in the absence of additional photosensitizer. The kinetic isotope effect (k H /k D ) was changed from 3.6 (under darkness) to 1.1 when irradiated by visible light, which indicated that the C-H functionalization step was the rate determining step under darkness and significantly accelerated by the irradiation of visible light. Finally the synthesis of ortho tetra-substituted vinylarene atropisomers with high enantiospecificity was realized via this protocol.