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CC BY-NC-ND 4.0 · Synthesis
DOI: 10.1055/a-1902-5592
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Catalytic hydrophosphination of allenes using an iron(II) β-diketiminate complex

Callum Woof
1   Department of Chemistry, University of Bath, Bath, United Kingdom of Great Britain and Northern Ireland (Ringgold ID: RIN1555)
,
Thomas Linford-Wood
1   Department of Chemistry, University of Bath, Bath, United Kingdom of Great Britain and Northern Ireland (Ringgold ID: RIN1555)
,
Mary Mahon
1   Department of Chemistry, University of Bath, Bath, United Kingdom of Great Britain and Northern Ireland (Ringgold ID: RIN1555)
,
Ruth Webster 
2   Department of Chemistry, University of Bath, Bath, United Kingdom of Great Britain and Northern Ireland (Ringgold ID: RIN1555)
3   University of Bath, University of Bath, Bath, United Kingdom of Great Britain and Northern Ireland (Ringgold ID: RIN1555)
› Author AffiliationsSupported by: Engineering and Physical Sciences Research Council
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A rare study into the catalytic hydrophosphination of allenes is reported. Employing an Fe(II) ß-diketiminate pre-catalyst, the reaction of HPPh2 proceeds with a range of aryl- and alkyl allenes. For arylallenes the E-vinyl product formed as the major species, while the 1,1-disubstituted alkene is formed in a larger ratio than the Z-vinyl product (e.g. 6 : 3 : 1 as E : 1,1 : Z). Use of H2PPh results in good yields of the 1,1-disubstituted alkene, where the resultant secondary phosphine product does not undergo further reaction. We postulate a catalytic cycle based on spectroscopic data. Employing an [Fe(salen)]2-μ-oxo pre-catalyst leads to phosphine dehydrocoupling rather than hydrophosphination.



Publication History

Received: 14 June 2022

Accepted after revision: 14 July 2022

Accepted Manuscript online:
18 July 2022

© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/).

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