Hydrogenations without hydrogen: titania photocatalyzed reductions of maleimides and aldehydes

David W. Manley; Luca Buzzetti; Andrew MacKessack-Leitch; John C. Walton

doi:10.3390/molecules190915324

Hydrogenations without hydrogen: titania photocatalyzed reductions of maleimides and aldehydes

David W. Manley, Luca Buzzetti, Andrew MacKessack-Leitch, John C. Walton^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	15324-15338
Number of pages	15
Journal	Molecules
Volume	19
Issue number	9
DOIs	https://doi.org/10.3390/molecules190915324
Publication status	Published - 24 Sept 2014

Keywords

Photocatalysis
Reduction
Titania
Maleimides
Aldehydes
Electron-deficient alkenes
Tertiary-amines
Radical-addition
Semiconductors
Photoaddition
Nanoparticles
Sensitizers
Alkylations
Complexes
Olefins

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10.3390/molecules190915324

Manley_2014_Mol_Hydrogenations
© 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/).
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Photocatalysis for Organic Synthesis: Photocatalysis for Organic Synthesis
Walton, J. C. (PI) & McBurney, R. T. (Researcher)
EPSRC
1/10/10 → 31/03/14
Project: Standard

Cite this

@article{54bc47708c234ef3abb39182a754e2ee,

title = "Hydrogenations without hydrogen: titania photocatalyzed reductions of maleimides and aldehydes",

abstract = "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.",

keywords = "Photocatalysis, Reduction, Titania, Maleimides, Aldehydes, Electron-deficient alkenes, Tertiary-amines, Radical-addition, Semiconductors, Photoaddition, Nanoparticles, Sensitizers, Alkylations, Complexes, Olefins",

author = "Manley, {David W.} and Luca Buzzetti and Andrew MacKessack-Leitch and Walton, {John C.}",

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

year = "2014",

month = sep,

day = "24",

doi = "10.3390/molecules190915324",

language = "English",

volume = "19",

pages = "15324--15338",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "9",

}

TY - JOUR

T1 - Hydrogenations without hydrogen

T2 - titania photocatalyzed reductions of maleimides and aldehydes

AU - Manley, David W.

AU - Buzzetti, Luca

AU - MacKessack-Leitch, Andrew

AU - Walton, John C.

N1 - The authors thank the EPSRC for funding (Grant EP/I003479/1) and the EPSRC National Mass Spectrometry Service, Swansea.

PY - 2014/9/24

Y1 - 2014/9/24

N2 - 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.

AB - 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.

KW - Photocatalysis

KW - Reduction

KW - Titania

KW - Maleimides

KW - Aldehydes

KW - Electron-deficient alkenes

KW - Tertiary-amines

KW - Radical-addition

KW - Semiconductors

KW - Photoaddition

KW - Nanoparticles

KW - Sensitizers

KW - Alkylations

KW - Complexes

KW - Olefins

U2 - 10.3390/molecules190915324

DO - 10.3390/molecules190915324

M3 - Article

SN - 1420-3049

VL - 19

SP - 15324

EP - 15338

JO - Molecules

JF - Molecules

IS - 9

ER -

Hydrogenations without hydrogen: titania photocatalyzed reductions of maleimides and aldehydes

Abstract

Keywords

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Projects

Photocatalysis for Organic Synthesis: Photocatalysis for Organic Synthesis

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