Intramolecular hydroformylation of allyldiphenylphosphine using a monodentate phosphorus diamide based rhodium catalyst: An NMR study

The stepwise intramolecular hydroformylation reaction of allyldiphenylphosp hine using a monodentate phosphorus diamide based rhodium catalyst has been studied using NMR spectroscopy. Reaction of the rhodium-hydride complex HR hL3CO (L = triethylbiuretphenylphosphorus diamide) with allyldiphenylphosph ine results in the formation of HRhL2-(allylPPh(2))CO. This compound underg oes hydride migration to form a cyclic rhodium-alkyl complex. When carbon m onoxide is added to this complex, ligand exchange and CO insertion occur, l eading to the formation of the cyclic rhodium-acyl complex Rh(CO)CH2CH2CH2P Ph2L(CO)(2). Addition of hydrogen completes the cycle forming the coordinat ed hydroformylated allyldiphenylphosphine ligand. The aldehyde-functionaliz ed phosphine ligand is hydrogenated to the corresponding alcohol.