title: Synthesis of binaphthyl based phosphine and phosphite ligands.
abstract: The development of large scale synthesis of enantiopure and thermally stable (R)- and (S)-BINOL molecules constitutes a key milestone in the field of asymmetric catalysis. Particularly, a great variety of chiral binaphthyl-based phosphorus compounds, herein represented by phosphite and phosphine classes, have earned considerable relevance due to their versatility as ligands in enantioselective metal-catalysed reactions, allowing the preparation of optically active products with the desired enantiopurity. This review highlights the most relevant concepts and accounts regarding general synthetic procedures for binaphthyl-based mono- and bidentate phosphites and phosphines. Furthermore, the search for environmentally benign chemical catalytic processes compelled us to also give special attention to the functionalisation of binaphthyl-based phosphorus ligands for use in alternative reaction media. When available, a critical selection of their applications in catalysis is briefly assessed.
authors.affiliation: Departamento de Química, Universidade de Coimbra, Rua Larga, 3004-535, Coimbra, Portugal. mmpereira@qui.uc.pt
authors.forename: Mariette M
authors.initials: MM
authors.lastname: Pereira
authors.forename: Mário J F
authors.initials: MJ
authors.lastname: Calvete
authors.forename: Rui M B
authors.initials: RM
authors.lastname: Carrilho
authors.forename: Artur R
authors.initials: AR
authors.lastname: Abreu
mesh_terms: D008024:Ligands; D009284:Naphthols / Q000737:chemistry*; D010720:Phosphines / Q000138:chemical synthesis / Q000737:chemistry*; D017905:Phosphites / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C406944:BINOL, naphthol; D008024:Ligands; D009284:Naphthols; D010720:Phosphines; D017905:Phosphites; C044646:phosphine