Markovnikov versus anti-Markovnikov hydrophosphination: Divergent reactivity using an iron(II) β-diketiminate pre-catalyst

Andrew King, Kimberley Gallagher, Mary F. Mahon, Ruth L. Webster

Research output: Contribution to journalArticle

13 Citations (Scopus)
41 Downloads (Pure)

Abstract

The ability to tune between different regioselectivities using a common pre-catalyst is an unusual yet highly desirable process. Here, we report the use of an iron(II) pre-catalyst that can be used to synthesize vinyl phosphines in a Markovnikov-selective manner in benzene, whereas a simple change to dichloromethane as the reaction solvent leads to the Z-selective anti-Markovnikov product. Preliminary mechanistic studies are reported that suggest Markovnikov selectivity is a radical-mediated process, whereas the anti-Markovnikov selectivity is not radical in nature but is due to a change in oxidation state.
Original languageEnglish
Pages (from-to)9039-9043
JournalChemistry - A European Journal
Volume23
Issue number38
Early online date19 Jun 2017
DOIs
Publication statusPublished - 6 Jul 2017

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