Unconventional Titania photocatalysis: direct deployment of carboxylic acids in alkylations and annulations

David Manley; Roy Thomas McBurney; Phillip Miller; Russell, F. Howe; Shona Rhydderch; John Christopher Walton

doi:10.1021/ja306168h

Unconventional Titania photocatalysis: direct deployment of carboxylic acids in alkylations and annulations

David Manley, Roy Thomas McBurney, Phillip Miller, Russell, F. Howe, Shona Rhydderch, John Christopher Walton^*

^*Corresponding author for this work

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

Abstract

Under dry, anaerobic conditions, TiO₂photocatalysis of carboxylic acid precursors resulted in carbon−carbon bond-forming processes. High yields of
dimers were obtained from TiO₂treatment of carboxylic acids alone. On inclusion of electron-deﬁcient alkenes, eﬃcient alkylations were achieved with methoxymethyl and phenoxymethyl radicals. In reactions with maleic anhydride or maleimides, phenoxyacetic acid produced chromenedione derivatives in addition to adducts. These photocatalytic reactions are simple and cheap to perform, and the TiO₂ is easily removed by ﬁltration. The anaerobic photocatalysis strategy oﬀers a range of synthetic possibilities.

Original language	English
Pages (from-to)	13580-13583
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	33
Early online date	10 Aug 2012
DOIs	https://doi.org/10.1021/ja306168h
Publication status	Published - 22 Aug 2012

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10.1021/ja306168h

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

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title = "Unconventional Titania photocatalysis: direct deployment of carboxylic acids in alkylations and annulations",

abstract = "Under dry, anaerobic conditions, TiO2 photocatalysis of carboxylic acid precursors resulted in carbon−carbon bond-forming processes. High yields ofdimers were obtained from TiO2 treatment of carboxylic acids alone. On inclusion of electron-deﬁcient alkenes, eﬃcient alkylations were achieved with methoxymethyl and phenoxymethyl radicals. In reactions with maleic anhydride or maleimides, phenoxyacetic acid produced chromenedione derivatives in addition to adducts. These photocatalytic reactions are simple and cheap to perform, and the TiO2 is easily removed by ﬁltration. The anaerobic photocatalysis strategy oﬀers a range of synthetic possibilities.",

author = "David Manley and McBurney, {Roy Thomas} and Phillip Miller and Howe, {Russell, F.} and Shona Rhydderch and Walton, {John Christopher}",

note = "Funding: The authors thank the EPSRC for funding (Grants EP/I003479/1 and EP/I00372X/1) and the EPSRC National Mass Spectrometry Service, Swansea.",

year = "2012",

month = aug,

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doi = "10.1021/ja306168h",

language = "English",

volume = "134",

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journal = "Journal of the American Chemical Society",

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publisher = "American Chemical Society (ACS)",

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TY - JOUR

T1 - Unconventional Titania photocatalysis

T2 - direct deployment of carboxylic acids in alkylations and annulations

AU - Manley, David

AU - McBurney, Roy Thomas

AU - Miller, Phillip

AU - Howe, Russell, F.

AU - Rhydderch, Shona

AU - Walton, John Christopher

N1 - Funding: The authors thank the EPSRC for funding (Grants EP/I003479/1 and EP/I00372X/1) and the EPSRC National Mass Spectrometry Service, Swansea.

PY - 2012/8/22

Y1 - 2012/8/22

N2 - Under dry, anaerobic conditions, TiO2 photocatalysis of carboxylic acid precursors resulted in carbon−carbon bond-forming processes. High yields ofdimers were obtained from TiO2 treatment of carboxylic acids alone. On inclusion of electron-deﬁcient alkenes, eﬃcient alkylations were achieved with methoxymethyl and phenoxymethyl radicals. In reactions with maleic anhydride or maleimides, phenoxyacetic acid produced chromenedione derivatives in addition to adducts. These photocatalytic reactions are simple and cheap to perform, and the TiO2 is easily removed by ﬁltration. The anaerobic photocatalysis strategy oﬀers a range of synthetic possibilities.

AB - Under dry, anaerobic conditions, TiO2 photocatalysis of carboxylic acid precursors resulted in carbon−carbon bond-forming processes. High yields ofdimers were obtained from TiO2 treatment of carboxylic acids alone. On inclusion of electron-deﬁcient alkenes, eﬃcient alkylations were achieved with methoxymethyl and phenoxymethyl radicals. In reactions with maleic anhydride or maleimides, phenoxyacetic acid produced chromenedione derivatives in addition to adducts. These photocatalytic reactions are simple and cheap to perform, and the TiO2 is easily removed by ﬁltration. The anaerobic photocatalysis strategy oﬀers a range of synthetic possibilities.

U2 - 10.1021/ja306168h

DO - 10.1021/ja306168h

M3 - Article

C2 - 22867432

SN - 0002-7863

VL - 134

SP - 13580

EP - 13583

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 33

ER -

Unconventional Titania photocatalysis: direct deployment of carboxylic acids in alkylations and annulations

Abstract

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Photocatalysis for Organic Synthesis: Photocatalysis for Organic Synthesis

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