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. 2014 Feb 10;356(2-3):603-608.
doi: 10.1002/adsc.201300787. Epub 2014 Feb 2.

A Convenient Synthetic Protocol to 1,2-Bis(dialkylphosphino)ethanes

Laurence R Doyle  1 , Alex Heath  1 , Choon Heng Low  1 , Andrew E Ashley  1
Affiliations

A Convenient Synthetic Protocol to 1,2-Bis(dialkylphosphino)ethanes

Laurence R Doyle et al. Adv Synth Catal. .

Abstract

1,2-Bis(dialkylphosphino)ethanes are readily prepared from the parent phosphine oxides, via a novel sodium aluminium hydride/sodium hydride reduction protocol of intermediate chlorophosphonium chlorides. This approach is amenable to multi-gram syntheses, utilises readily available and inexpensive reagents, and benefits from a facile non-aqueous work-up in the final reductive step.

Keywords: aluminium; hydrides; phosphane ligands; reduction; synthetic methods.

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Figures

Scheme 1
Scheme 1
Previous synthetic routes to Me2PCH2CH2PMe2 (dmpe; 3a).
Scheme 2
Scheme 2
Synthesis of Me2PCH2CH2PMe2 (dmpe; 3a): (i) 6 equiv. MeMgCl/THF; (ii) 0.5 equiv. ClCH2CH2Cl, reflux then K2CO3(aq.); (iii) 2.1 equiv. (COCl)2/CH2Cl2.
Scheme 3
Scheme 3
Novel synthesis of 1,2-bis(di-tert-butylphosphinomethyl)pyridine (3f); (i) 6 equiv. t-BuLi/Et2O/2 equiv. HP(=O)(OEt)2; (ii) excess (COCl)2/CH2Cl2; (iii) 2 equiv. NaAlH4/4 equiv. NaH/THF.
See this image and copyright information in PMC

References

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