Activation and Functionalization of Organic Disulfides by Bis(Perfluoroalkyl) Complexes of Nickel(II)

High Resolution Image Download MS PowerPoint Slide The [(MeCN) 2 Ni(R f ) 2 ] platform was used to study the oxidative addition of 8,8′-diquinolyl disulfide. The oxidative addition proceeds to afford [Ni(R f ) 2 (SR) 2 ] intermediates, which then eliminate R aryl -S-R fluoroalkyl products through consecutive carbon–sulfur bond-forming steps. The high-valent states of the nickel complexes are required to reductively eliminate the cross-coupled product, and it was shown through stoichiometric reactions that both the singly and doubly oxidized states can trigger the S–C perfluoroalkyl bond forming reductive eliminations. These results show that such metal-mediated coupling reactions are viable and worthy of consideration in new methods development.