title: Synthesis of phosphaguanidines by hydrophosphination of carbodiimides with phosphine boranes.
abstract: The direct addition of anionic secondary phosphine boranes to carbodiimides yields both chiral and achiral phosphaguanidine boranes under ambient temperature conditions. An analogous preparation of menthol-derived phosphinite boranes is also described. These products can be deborinated to give the corresponding phosphines, and subsequently oxidized to give phosphine oxides. The robustness of this method was further demonstrated in the synthesis of structurally novel cyclic phosphaguanidines.
authors.affiliation: Chemical Development, Boehringer-Ingelheim Pharmaceuticals, Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Carl A
authors.initials: CA
authors.lastname: Busacca
authors.forename: John A
authors.initials: JA
authors.lastname: Milligan
authors.forename: Eakkaphon
authors.initials: E
authors.lastname: Rattanangkool
authors.forename: Cyrus
authors.initials: C
authors.lastname: Ramavarapu
authors.forename: Anji
authors.initials: A
authors.lastname: Chen
authors.forename: Anjan K
authors.initials: AK
authors.lastname: Saha
authors.forename: Zhibin
authors.initials: Z
authors.lastname: Li
authors.forename: Heewon
authors.initials: H
authors.lastname: Lee
authors.forename: Steven J
authors.initials: SJ
authors.lastname: Geib
authors.forename: Guijun
authors.initials: G
authors.lastname: Wang
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
authors.forename: Peter
authors.initials: P
authors.lastname: Wipf
mesh_terms: D001880:Boranes / Q000737:chemistry*; D002234:Carbodiimides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D019791:Guanidine / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001880:Boranes; D002234:Carbodiimides; D010087:Oxides; D010720:Phosphines; D019791:Guanidine