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Issue 35, 2011
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Chiral palladacycles based on resorcinol monophosphite ligands: the role of the meta-hydroxyl in ligand C–H activation and catalysis

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Abstract

The reactions of a range of chiral resorcinol monophosphite ligands with [PdCl2(NCMe)2] was investigated in order to establish whether the meta-hydroxyl function was involved in the orthometallation processes. These ligands underwent facile orthopalladation at room temperature in the presence of Et3N, whilst the equivalent hydroxyl-free analogues needed more forcing conditions to induce orthometallation. When the hydroxyl function was replaced by a similar sized methyl group no orthometallation occurred, even on heating. Furthermore the hydroxyl group influences both the structure and isomerism in the resultant palladacycles viahydrogen bonding to adjacent chloride ligands. Similarly, the hydroxyl function leads to higher enantiocontrol in the asymmetric allylation of benzaldehyde with allyl tributyltin. Representative examples of the ligands and the palladium complexes obtained were characterised by single crystal X-ray diffraction.

Graphical abstract: Chiral palladacycles based on resorcinol monophosphite ligands: the role of the meta-hydroxyl in ligand C–H activation and catalysis

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Publication details

The article was received on 02 Mar 2011, accepted on 21 Jun 2011 and first published on 05 Aug 2011


Article type: Paper
DOI: 10.1039/C1DT10357A
Citation: Dalton Trans., 2011,40, 9042-9050

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    Chiral palladacycles based on resorcinol monophosphite ligands: the role of the meta-hydroxyl in ligand C–H activation and catalysis

    R. B. Bedford, Y. Chang, M. F. Haddow and C. L. McMullin, Dalton Trans., 2011, 40, 9042
    DOI: 10.1039/C1DT10357A

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