A commercially available iron compound, [CpFe(CO)] (1) (Cp = η-CH), is an efficient catalyst for the double hydrophosphination of terminal aryl alkynes with diphenylphosphine under visible light irradiation or thermal conditions with a reduction of reaction times of up to two orders of magnitude for some substrates over literature reports. The 1,2-bis(diphenylphosphino)ethane products generated in these reactions are readily isolated in high yields.
The ubiquitous half-sandwich iron complex [CpFe(CO) Me] (Cp=η -C H ) appears to be a catalyst for α-phosphinidene elimination from primary phosphines. Dehydrocoupling reactions provided initial insight into this unusual reaction mechanism, and trapping reactions with organic substrates gave products consistent with an α elimination mechanism, including a rare example of a three-component reaction. The substrate scope of this reaction is consistent with generation of a triplet phosphinidene. In all, this study presents catalytic phosphinidene transfer to unsaturated organic substrates.
Phosphinidenes are powerful synthetic reagents used to prepare important organophosphorus compounds, but historically, their generation has been stoichiometric. A simple iron compound, [CpFeMe(CO)2], can catalytically transfer a phosphinidene fragment to unsaturated fragments with loss of hydrogen. This apparent α‐phosphinidene elimination reaction may enable more green syntheses of organophosphines. More information can be found in the Communication by R. Waterman et al. on page 2554.
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