Solvent- and catalyst-free regioselective hydrophosphanation of alkenes

YANINA MOGLIE; FRANCISCO ALONSO; GABRIEL RADIVOY; MIGUEL YUS

Alicante

Jornada; XV Jornadas de Investigación Departamental San Alberto Magno; 2012

Universidad de Alicante

Organophosphorus compounds are widely used in the chemical, agrochemical, and pharmaceutical industries. In particular, phosphane ligands are very important in homogeneous and asymmetric catalysis. In recent years, increasing attention has also been devoted to the design of metal-phosphane complexes with anticancer activity, as potential substitutes of the current platinum drugs. Some transition-metals such as platinum, lanthanocenes, ytterbium, copper, iron, nickel and palladium complexes were applied in the direct addition of phosphanes to alkenes (hydrophosphanation). The formation of the anti-Markovnikov products is a common feature for all these metal-catalysed strategies. Notwithstanding the utility of the aforementioned methods, expensive and, in some cases, toxic catalytic systems are applied often under harsh conditions. The oxidation of the resulting phosphane to the corresponding phosphane oxide is another inconvenience commonly encountered, which can be enhanced by the presence of the metal. Our interest in the transition-metal catalysed addition of Het-H bonds across carbon-carbon multiple bonds led us to the discovery of the uncatalysed addition of secondary phosphanes to alkenes under solvent-free conditions.