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Issue 35, 2011
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Tuning ligand structure in chiral bis(phosphite) and mixed phosphite–phosphinite PCP-palladium pincer complexes

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Abstract

A range of chiral resorcinol bis(phosphite) and phosphite–phosphinite ligands were produced and their propensity to form palladiumPCP-pincer complexes examined. The ease of base-assisted C–H palladation of the ligands falls in the order bis(phosphinite) > phosphite–phosphinite > bis(phosphite). The catalytic activity of the complexes in the asymmetric allylation of benzaldehyde with allyl tributyltin was examined and it was found that, contrary to expectations, ligands with 3,3′-disubstituted BINOL residues show poorer activity and stereoselectivity than unsubstituted BINOL analogues. In addition the order of activity of the pincer complexes was established as bis(phosphite) > phosphite–phosphinite > bis(phosphinite). Crystal structures of representative examples of a 3,3′-disubstituted BINOL, mono- and bis(phosphite) ligands based on 2,4-di-tert-butyl resorcinol and Pd complexes of two of the chiral complexes are presented.

Graphical abstract: Tuning ligand structure in chiral bis(phosphite) and mixed phosphite–phosphinite PCP-palladium pincer complexes

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Article information


Submitted
02 Mar 2011
Accepted
21 Jun 2011
First published
05 Aug 2011

Dalton Trans., 2011,40, 9034-9041
Article type
Paper

Tuning ligand structure in chiral bis(phosphite) and mixed phosphite–phosphinite PCP-palladium pincer complexes

R. B. Bedford, Y. Chang, M. F. Haddow and C. L. McMullin, Dalton Trans., 2011, 40, 9034
DOI: 10.1039/C1DT10356C

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