Direct Aminophosphonylation of aldehydes catalyzed by cyclopentadienyl ruthenium(II) complexes. Issue 15 (12th April 2018)

• Record Type: Journal Article
• Authors: Cabrita, Ivânia R.; Sousa, Sara C.A.; Florindo, Pedro R.; Fernandes, Ana C.
• Is Part Of: Tetrahedron. Volume 74:Issue 15(2018)
• Page Start: 1817
• Page End: 1825
• Publication Date: 2018-04-12
• Subjects: Aminophosphonylation -- Aldehydes -- α-Aminophosphonates -- Ruthenium complexes; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.02.047
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: This work reports a novel method for the direct aminophosphonylation of aldehydes catalyzed by cyclopentadienyl ruthenium(II) complexes. The system HP(O)(OEt)2 /[CpRu(PPh3 )2 Cl] was very efficient for the aminophosphonylation of aldehydes with primary and secondary amines, producing the corresponding α-aminophosphonates in good to excellent yields. This novel method has several advantages including the use of a small amount of catalyst (0.5 mol%), high chemoselectivity, solvent-free conditions and application of the catalyst [CpRu(PPh3 )2 Cl] for at least 12 cycles with excellent activity. Graphical abstract: Highlights: [CpRu(PPh3 )2 Cl] is a very efficient catalyst for the direct aminophosphonylation of aldehydes. The catalyst [CpRu(PPh3 )2 Cl] can be used for at least 12 catalytic cycles with excellent activity. The reactions can be performed under solventfree conditions.