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Reduction of carbon–carbon double bonds is reported using a three-coordinate iron(II) β-diketiminate pre-catalyst. The reaction is believed to proceed via a formal transfer hydrogenation using poly(methylhydrosiloxane), PMHS, as the hydride donor and a bio-alcohol as the proton source. The reaction proceeds well using n-butanol and ethanol, with n-butanol being used for substrate scoping studies. Allyl arene substrates, styrenes and aliphatic substrates all undergo reduction at room temperature. Unfortunately, clean transfer of a deuterium atom using D-alcohol does not take place, indicating a complex catalytic mechanism. However, changing the deuterium source to D-aniline gives close to complete regioselectivity for mono-deuteration of the terminal position of the double bond. Finally, we demonstrate that efficient dehydrocoupling of alcohol and PMHS can be undertaken using the same pre-catalyst, giving high yields of H2 within 30 minutes at room temperature.
|Early online date||11 Mar 2021|
|Publication status||Published - 7 Apr 2021|
FingerprintDive into the research topics of 'Room temperature iron catalyzed transfer hydrogenation using n-butanol and poly(methylhydrosiloxane)'. Together they form a unique fingerprint.
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EC Fellowship - Cast Iron Catalysis: New Protocols for the Synthesis of Carbon-Phosphorus Bonds
Engineering and Physical Sciences Research Council
3/12/17 → 2/03/24
Project: Research council