Jump to main content
Jump to site search

Issue 3, 2013
Previous Article Next Article

NOBIN-based phosphoramidite and phosphorodiamidite ligands and their use in asymmetric nickel-catalysed hydrovinylation

Author affiliations

Abstract

Phosphoramidite and P-stereogenic phosphorodiamidite ligands derived from (Sa)-2-phenylamino-2′-hydroxy-1,1′-binaphthyl (N-Ph-NOBIN) and bis(1-phenyl-ethyl)amine were synthesised, fully characterised, and the absolute configuration of the stereogenic phosphorus atoms was assigned. The phosphoramidite ligand L2 features three non-bridged substituents at phosphorus comprising the bis(1-phenylethyl)amine and two NOBIN moieties. The NOBIN units are bound to the phosphorus through the oxygen atoms with two pendant nitrogen atoms. In the Ni-catalysed hydrovinylation of styrene no conversion was observed with the phosphorodiamidites, while the phosphoramidite ligands led to active catalysts with a marked co-operative effect on selectivities. Whereas the racemic product was obtained with the (Sa,Sa,SC,SC) diastereomer, the (Sa,Sa,RC,RC) diastereomer proved to be one of the best ligands for this reaction, leading to almost perfect selectivity and ees of up to 91%.

Graphical abstract: NOBIN-based phosphoramidite and phosphorodiamidite ligands and their use in asymmetric nickel-catalysed hydrovinylation

Back to tab navigation

Supplementary files

Publication details

The article was received on 19 Sep 2012, accepted on 30 Oct 2012 and first published on 01 Nov 2012


Article type: Paper
DOI: 10.1039/C2CY20657A
Catal. Sci. Technol., 2013,3, 589-594

  •   Request permissions

    NOBIN-based phosphoramidite and phosphorodiamidite ligands and their use in asymmetric nickel-catalysed hydrovinylation

    M. Schmitkamp, W. Leitner and G. Franciò, Catal. Sci. Technol., 2013, 3, 589
    DOI: 10.1039/C2CY20657A

Search articles by author

Spotlight

Advertisements