Hydrogenations without hydrogen : titania photocatalyzed reductions of maleimides and aldehydes

A mild procedure for the reduction of electron-deficient alkenes and carbonyl compounds is described. UVA irradiations of substituted maleimides with dispersions of titania (Aeroxide P25) in methanol/acetonitrile (1:9) solvent under dry anoxic conditions led to hydrogenation and production of the corresponding succinimides. Aromatic and heteroaromatic aldehydes were reduced to primary alcohols in similar titania photocatalyzed reactions. A mechanism is proposed which involves two proton-coupled electron transfers to the substrates at the titania surface.

Citation

Manley , D W , Buzzetti , L , MacKessack-Leitch , A & Walton , J C 2014 , ' Hydrogenations without hydrogen : titania photocatalyzed reductions of maleimides and aldehydes ' , Molecules , vol. 19 , no. 9 , pp. 15324-15338 . https://doi.org/10.3390/molecules190915324

Publication

Molecules

Status

Peer reviewed

DOI

https://doi.org/10.3390/molecules190915324

ISSN

1420-3049

Type

Journal article

Rights

© 2014 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).

Description

The authors thank the EPSRC for funding (Grant EP/I003479/1) and the EPSRC National Mass Spectrometry Service, Swansea.

Collections

University of St Andrews Research

URI

http://hdl.handle.net/10023/5796