Issue 7, 2021

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

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)

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
09 Dec 2020
Accepted
10 Mar 2021
First published
11 Mar 2021
This article is Open Access
Creative Commons BY-NC license

Green Chem., 2021,23, 2703-2709

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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