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Issue 7, 2021
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Room temperature iron catalyzed transfer hydrogenation using n-butanol and poly(methylhydrosiloxane)

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Abstract

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.

Graphical abstract: Room temperature iron catalyzed transfer hydrogenation using n-butanol and poly(methylhydrosiloxane)

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Submitted
09 Dec 2020
Accepted
10 Mar 2021
First published
11 Mar 2021

This article is Open Access

Green Chem., 2021,23, 2703-2709
Article type
Paper

Room temperature iron catalyzed transfer hydrogenation using n-butanol and poly(methylhydrosiloxane)

T. G. Linford-Wood, N. T. Coles and R. L. Webster, Green Chem., 2021, 23, 2703
DOI: 10.1039/D0GC04175K

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