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

Linford-Wood, Thomas G., Coles, Nathan T. ORCID: https://orcid.org/0000-0001-6190-9080 and Webster, Ruth L. 2021. Room temperature iron catalyzed transfer hydrogenation using n-butanol and poly(methylhydrosiloxane). Green Chemistry 23 (7) , pp. 2703-2709. 10.1039/D0GC04175K

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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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Royal Society of Chemistry
ISSN:	1463-9262
Date of First Compliant Deposit:	4 December 2024
Date of Acceptance:	10 March 2021
Last Modified:	04 Dec 2024 10:17
URI:	https://orca.cardiff.ac.uk/id/eprint/173583

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