The role of organonickel reagents in organophosphorus chemistry

Abstract Organonickel reagents are widely used for the obtaining of the organophosphorus compounds from different phosphorus sources including elemental white phosphorus, phosphorus trichloride and phosphine PH3. In particular, new highly efficient and environmentally friendly methods for preparation of organophosphorus compounds bearing phosphorus–carbon bonds have been elaborated using the electrochemically generated organonickel complexes. The synthetic application of the developed techniques towards the formation of wide range of practically important primary, secondary and tertiary organophosphines, with a special focus on unsymmetrical PH phosphines, is disclosed. The mechanistic pathways and the structure of the assumed intermediates formed on some key stages of the overall process are presented for discussion. The elaborated methods operate on the electrochemical techniques with combination of coordination chemistry principles and are considered as an efficient alternative to the more common methods.