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Issue 6, 2014
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Synthesis and characterisation of novel o-xylene-based P,E ligands

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Abstract

A range of novel hybrid ligands of the type, o-C6H4(CH2PBut2)(CH2E) (E = P(C6F5)2, SBut, SPh, S(O)But, NR2, SiPh2H), have been synthesised in two or three steps from the common substrate, o-C6H4{CH2PBut2(BH3)}(CH2Cl). The initial step involved treatment of the substrate with the appropriate nucleophilic reagent, or preparation of a Grignard reagent from o-C6H4{CH2PBut2(BH3)}(CH2Cl) and reaction with the appropriate electrophile. In most cases, this versatile strategy produced air-stable crystalline ligand precursors. Phosphine deprotection was achieved via one of three methods, dependent upon the properties of the second functional group. An alternative synthesis of the known ligand, o-C6H4(CH2PBut2)(CH2PPh2), is also presented.

Graphical abstract: Synthesis and characterisation of novel o-xylene-based P,E ligands

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Publication details

The article was received on 12 Nov 2013, accepted on 11 Dec 2013 and first published on 13 Dec 2013


Article type: Paper
DOI: 10.1039/C3OB42244E
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 956-964
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    Synthesis and characterisation of novel o-xylene-based P,E ligands

    K. M. Allan and J. L. Spencer, Org. Biomol. Chem., 2014, 12, 956
    DOI: 10.1039/C3OB42244E

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